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D-Biotin
Cas No: 58-85-5
No Data 1 Gram Metric Ton/Day Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Vitamin H 98%
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USD $ 100.0-100.0 / Kilogram 1 Kilogram 200 Metric Ton/Year EXCELLENT HEALTH PRODUCTS CO.,LTD Contact Supplier
D-Biotin
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Fast Shipping Human supplement 99% purity Vitamin B7 / D-biotin / Vitamin H Powder
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USD $ 77.0-589.0 / Kilogram 2 Kilogram 1000 Metric Ton/Month Xi'an Quanao Biotech Co., Ltd. Contact Supplier
Pharmaceutical Grade CAS 58-85-5 D-Biotin / Vitamin H/Biotin with GMP Standard for Vasodilator
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High purity D-Biotin Vitamin H
Cas No: 58-85-5
USD $ 2600.0-2800.0 / Kilogram 1 Kilogram 50 Metric Ton/Month Tianjin YR Chemspec Technology Co.,Ltd. Contact Supplier
Topsale BIOTIN, D-BIOTIN, VITAMIN H 99%
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USD $ 1.0-1.0 / Kilogram 1 Kilogram 100 Kilogram/Month Shanghai Upbio Tech Co.,Ltd Contact Supplier

58-85-5 Usage

Toxicity

Toxicity of biotin seems to be low. Treatment of seborrheic dermatitis with high doses of biotin did not detect abnormal protein metabolism or genetic errors and other metabolic abnormalities. Animal experiments also show that biotin toxicity is low.

Description

D-Biotin, also called Vitamin H, is a colorless, water-soluble member of the group of B-vitamins. Formerly it was known as vitamin H or coenzyme R. It has many benefits for the hair, skin, and nails. It is composed of a ureido ring fused with a tetrahydrothiophene ring. A valeric acid substituent is attached to one of the carbon atoms of the tetrahydrothiophene ring. Biotin is a coenzyme for carboxylase enzymes, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. Subclinical deficiency of Biotin can cause mild symptoms, such as hair thinning or skin rash typically on the face. Thus, This product is recommended for general food fortification and dietary supplement applications. Generally, D-Biotin can be used for baby food and dietetics, for solid and liquid pharmaceutical preparations, for cosmetic preparations, and for use in the fermentation industry.

Originator

Biotin,Solgar

References

https://www.ulprospector.com/en/na/PersonalCare/Detail/473/317131/D-Biotin https://en.wikipedia.org/wiki/Biotin http://www.medicalnewstoday.com/articles/219718.php http://www.selleckchem.com/products/biotin-vitamin-b7.html

Applications

As a feed additive, it is mainly used for poultry and sow feed. Usually the premixed mass fraction is 1%-2%. It is nutritional supplement. According to China GB2760-90 regulations, it could be used as a food industry as a processing aid. It has physiological functions to prevent skin diseases and promote lipid metabolism and so on. It is carboxylase coenzyme, involved in many carboxylation reactions, and is an important coenzyme in the metabolism of sugar, protein and fat. It is used as food fortifier. It is used for infant food with amount of 0.1~0.4mg/kg, in the drinking liquid 0.02~0.08mg/kg. It could be used for labeling proteins, antigens, antibodies, nucleic acids (DNA, RNA) and so on.

Physicochemical property

Biotin is widely distributed in animals and plants, and the natural presence of biotin is mainly in the form of binding with other molecules. The biochemical structure of biotin includes a shuttle chain containing five carbon atoms and two five-membered heterocycles. In vivo the shuttle of the side chain binds with lysine s residue of enzyme protein, playing a role of coenzyme. Biotin may have 8 different isomers, of which only D-biotin has biological activity. Under normal circumstances, biotin is quite stable, only in the strong acid, alkali, formaldehyde and UV treatment will be destroyed. Biotin is the carrier of carboxyl in the carboxylation reaction required large ATP. The carboxyl group is temporarily bound to a nitrogen atom on the bicyclic ring system of biotin, such as in the reaction of pyruvate carboxylase catalyzing the pyruvate carboxylation of oxaloacetate. Figure1: The structural formula of the biotin molecule

Definition

ChEBI: An organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thieno[3,4-d]imidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. The parent of the class of biotins.

Therapeutic Function

Vitamin

Biotin deficiency

Biotin deficiency appears to be rare, but some groups may be more susceptible.Biotin supplements are widely available but rarely necessary. A deficiency can lead to: Hair loss A scaly red rash around the eyes, nose, mouth, and genitals Cracks in the corner of the mouth Sore tongue that may be magenta in color Dry eyes Loss of appetite Other symptoms may include: Depression Lethargy and fatigue Hallucinations Insomnia Numbness and tingling in the hands and feet Impaired immune function and increased susceptibility to infections Pregnant women appear to break down biotin more quickly, and this may lead to a marginal deficiency. Symptoms have not been observed, but such a deficiency could lead to developmental problems for the fetus.

Manufacturing Process

4-Carbomethoxy-2-(4,5-dihydrothiophen-3(2H)-one)valeric acid methyl ester was prepared from 4,5-dihydrothiophene as it was described in Baker et al., J. Org. Chem., 12, 167 (1947). A solution of 60.0 g (0.182 mole) this ester in 550 ml absolute ethanol was treated with 91.6 g (1.45 moles) of ammonium formate. The reaction mixture refluxed for 5.0 hours. Then it was cooled, concentrated, and partitionated in a separatory funnel between 200 ml dichloromethane and 150 ml water. The aqueous phase was extracted three times with 50 ml portions of dichloromethane. The organic extracts were collected, dried over anhydrous sodium sulfate, and evaporated. 50 g (0.182 mole, 100%) 3-amino-4- carbomethoxy-2,5-dihydro-2-thiophenevaleric acid methyl ester was obtained as a colorless oil. To a solution of 27.3 g (1 mole) of 3-amino-4-carbomethoxy-2,5-dihydro-2- thiophenevaleric acid methyl ester in 250 ml dry methanol was added 4.0 g (0.1 mole) of sodium hydroxide pellets. The reaction mixture was refluxed 4.0 hrs, cooled and concentrated to a volume of 50 ml. The residue was taken up in 80 ml dichloromethane and transfered to a separatory funnel. After the addition of 150 ml of 10% by weight aqueous sodium bicarbonate solution, the aqueous layer was extracted twice with 50 ml portions of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and evaporated to yield 6.4 g (0.0234 mole) of recovered starting material. The aqueous phase was adjusted to pH 1 with 6 N hydrochloric acid and extracted three times with 75 ml portions of dichloromethane. The organic phases were pooled, dried over anhydrous sodium sulfate, and evaporated to yield 18.3 g (0.071 mole, 71%) of 3- amino-4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid as a tan solid, upon trituration with pet. ether. The recovered starting material, 6.4 g (0.0234 mole) was dissolved in 70 ml dry methanol and treated with 1.0 g (0.025 mole) sodium hydroxide. The mixture was refluxed 5.0 hrs, cooled concentrated, and taken up in 80 ml dichloromethane. The organic phase was treated in a separatory funnel with 100 ml of 10% by weight aqueous sodium bicarbonate solution. The aqueous phase was extracted twice with 40 ml portions of dichloromethane. The aqueous phase was acidified to pH 1 with 6 N hydrochloric acid and extracted two times with 50 ml portions of dichloromethane. The organic phases were cooled, dried over anhydrous sodium sulfate, and evaporated to dryness to afford an additional 5.3 g (0.021 mole, 21%) of 3-amino-4-carbomethoxy- 2,5-dihydro-2-thiophenevaleric acid; m.p. 98°-102°C.

Content analysis

Accurately weighed the sample about 500mg, mixed with 100ml of water, plus phenolphthalein test solution (TS-167) a few drops, with 0.1mol/L sodium hydroxide solution slowly added to the suspension in continuous heating and stirring, until we got pink suspension. 0.1 mol/L sodium hydroxide per ml is equivalent to 24.43 mg biotin (C10Hl6N2O3S).

Uses

Growth factor present in minute amounts in every living cell. Plays an indispensable role in numerous naturally occurring carboxylation reactions. Occurs mainly bound to proteins or polypeptides. The richest sources are liver, kidney, pancreas, yeast, and milk. The biotin content of cancerous tumors is higher than that of normal tissue.

Brand name

Bioepiderm (Sterling Winthrop).

Safety Profile

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and SOx.

Chemical Properties

White powder

Uses

vasodilator

Purification Methods

D-(+)-Biotin crystallises from hot water in fine long needles with a solubility of 22 mg/100mL at 25o. Its solubility in 95% EtOH is 80 mg/100 mL at 25o. Its isoelectric point is at pH 3.5. Store solid and solutions under sterile conditions because it is susceptible to mould growth. [Confalone J Am Chem Soc 97 5936 1975, Wolf et al. J Am Chem Soc 67 2100 1945, Synthesis: Ohuri & Emoto Tetrahedron Lett 2765 1975, Harris et al. J Am Chem Soc 66 1756 1944.] The (+)-methyl ester has m 166-167o (from MeOH/Et2O), [] D 22 +57o (c 1, CHCl3) [du Vigneaud et al. J Biol Chem 140 643, 763 1941]; the (+)-S-oxide has m 200-203o, [] D 20 +130o (c 1.2, 0.1N NaOH) [Melville J Biol Chem 208 495 1954]; the SS-dioxide has m 274-275o(dec, 268-270o), and the SS-dioxide methyl ester has m 239-241o (from MeOH/Et2O) [Hofmann et al. J Biol Chem 141 207, 213 1941]. [Beilstein 27 III/IV 7979.]

Physiological function

Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids. It plays a role in the citric acid cycle, which is the process by which biochemical energy is generated during aerobic respiration. Biotin is a coenzyme for carboxylase enzymes, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. In addition, biotin is widely used throughout the biotechnology industry to conjugate proteins for biochemical assays. We need biotin about 100 to 300 micrograms per day. There is an antibiotic protein that could combine with biotin in the egg white egg. After combining, it cannot be absorbed by the digestive tract; resulting in animal biotin deficiency, at the same time loss of appetite, glossitis, dermatitis dermatitis, hair removal and so on. However, there is no case of biotin deficiency on human, probably because in addition to food sources, intestinal bacteria can also synthesize biotin. Biotin is a coenzyme of a lot of enzymes in the human body. It participates in the metabolism of aliphatic acid, carbohydrate, vitamin B12, folic acid and pantothenic acid; promoting synthesis of protein and urea, and also promoting excretion. Help fat, glycogen and amino acids for normal synthesis and metabolism in the human body; Promote the normal operation and growth of sweat glands, nerve tissue, bone marrow, male gonads, skin and hair, and reduce eczema, dermatitis symptoms; Prevent white hair and hair loss, contribute to the treatment of baldness; Relieve muscle pain; Promote synthesis and excretion of urea, purine synthesis and oleic acid biosynthesis; For the treatment of atherosclerosis, stroke, dyslipidemia, hypertension, coronary heart disease and blood circulation disorders.

Biotin and fat metabolism

As a coenzyme of phthalocyanine coenzyme A, Biotin is involved in the synthesis of fatty acids, catalyzing the formation of glycine CoA. The reaction is the first step in the synthesis of fatty acids, and then through the cytoplasmic multi-enzyme complex and fatty acid synthase synthesize palmitic acid from the phthalocyanine-CoA. In the prolongation of carbon chain in the fatty acid, the propanedio phthalide-ACP is involved in the reaction as a donor of the dicarbon unit, and the dipropyl phthalide-ACP is derived from the phthalide-CoA. It can be seen that biotin is necessary for the synthesis of fatty acids and the extension of carbon chains in fatty acid. Biotin deficiency can lead to abnormal lipid metabolism, resulting in changes of fatty acid composition in the body. In addition, synthesis of saturated fatty acid decreased, synthesis of triglyeeride increased, and fat in the liver and kidney increased by 2 to 5 times. Biotin-deficient diets increase the rate of desiccation of palmitic acid in liver tissue by five folds. Palmitic acid increased, at the same time stearic acid reduced. Biotin is also a necessary material for synthesis of long-chain unsaturated fatty acid and fatty acid metabolism. Biotin is also associated with the synthesis of acetylcholine and the metabolism of cholesterol. The lack of biotin reduces the ability of animals to synthesize arachidonic acid from linoleic acid, leading to the accumulation of linoleic acid in the body.

Distinguishing test

The warm water saturated solution of the sample could cause the drop of the bromine test solution (TS-46) to fade.

Side effect

Bursts of cystic acne of jaw and chin are the most common side effects of biotin. The specific reason is not very clear. And usually this symptom will disappear by itself after a few weeks. There are also some nutritional supplements who report that acne symptoms can be reduced when the dose is limited to 2500 micrograms or less. In short, the situation experienced by each person is slightly different. Life-threatening biotin is extremely rare. Eosinophilic pleural effusion is the only documented deadly case that causes a woman to die. She ingested a lot of biotin, along with vitamin B5. So far, it is unclear whether her death is caused by biotin, B5, or a mixture of both. Healthy adults are less likely to develop biotin deficiency. This disease is common in excessive consumption of avidin (which can be found in raw eggs), or people with skin or hair disorders (such as phenylketonuria). The symptoms of lacking biotin usually take several years to show. The study found that about 50% of pregnant women had a biotin deficiency problem. They lack a kind of enzyme to tell the body how to use biotin properly, which leads to a decline in metabolic function. Most physicians do not recommend biotin nutrition as a treatment because the trial for rats found that it had a risk of miscarriage and fetal defects. Biotin is often recommended as nourishment for the promotion of hair and nail health. Because of the impact on carbohydrates, it is also often used to control body weight. Biotin supplements are known for their beauty and metabolic effects. The recommended dose ranges from 3 micrograms to 5000 micrograms per day, depending on the specific use. The side effects are relatively rare, and it is relatively easy to control even if the side effects appear, so it is a safe nutritional supplements.

Food source

Liver Peanuts Yeast Whole-wheat bread Cheddar cheese Pork Salmon Sardines Avocado Raspberries Bananas Mushrooms Cauliflower Egg yolk Egg white reduces the effectiveness of biotin from egg yolk in the body because it binds biotin and prevents it from being absorbed. People who consume only egg white for many years without biotin supplementation have a slight risk of not getting enough vitamin B7. Processing food reduces levels of nutrients such as biotin, so raw cauliflower, for example, would provide more biotin than cooked cauliflower. A study published in Advances in Nutrition estimates biotic intake in North America and Western Europe at between 35 to 70 μg per day, or 143 to 287 mmol per day. According to Oregon State University, biotin is not known to cause toxic effects. People with hereditary disorders of biotin metabolism tolerate doses of up to 200,000 mcg per day without any problems. Individuals with no biotin metabolism disorder who took doses of 5,000 mcg per day for 24 months had no adverse effects. However, it is important to speak to a physician or dietitian before making any change to nutritional intake or using supplements.

Uses

vitamin B complex
InChI:InChI=1/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/p-1/t6-,7-,9+/m0/s1

58-85-5 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (B0463)  Biotin  >98.0%(T) 58-85-5 100mg 80.00CNY Detail
TCI America (B0463)  Biotin  >98.0%(T) 58-85-5 1g 299.00CNY Detail
TCI America (B0463)  Biotin  >98.0%(T) 58-85-5 5g 980.00CNY Detail
Alfa Aesar (A14207)  D-(+)-Biotin, 98+%    58-85-5 1g 547.0CNY Detail
Alfa Aesar (A14207)  D-(+)-Biotin, 98+%    58-85-5 5g 2390.0CNY Detail
Alfa Aesar (A14207)  D-(+)-Biotin, 98+%    58-85-5 10g 3945.0CNY Detail
Alfa Aesar (A14207)  D-(+)-Biotin, 98+%    58-85-5 25g 8547.0CNY Detail
Sigma-Aldrich (91827)  Biotin  certified reference material, TraceCERT® 58-85-5 91827-50MG 1,055.34CNY Detail
Sigma-Aldrich (PHR1233)  Biotin  pharmaceutical secondary standard; traceable to USP and PhEur 58-85-5 PHR1233-1G 952.15CNY Detail
Sigma-Aldrich (B1116000)  Biotin  European Pharmacopoeia (EP) Reference Standard 58-85-5 B1116000 1,880.19CNY Detail
Sigma-Aldrich (19606)  Biotin  tested according to Ph.Eur. 58-85-5 19606-1G-F 3,536.91CNY Detail
USP (1071508)  Biotin  United States Pharmacopeia (USP) Reference Standard 58-85-5 1071508-200MG 4,662.45CNY Detail

58-85-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name biotin

1.2 Other means of identification

Product number -
Other names FACTOR S

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-85-5 SDS

58-85-5Synthetic route

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; tin(IV) chloride at 150℃; under 300.03 Torr; for 3.5h; Temperature; Pressure; Reagent/catalyst; Autoclave;97.5%
(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione
28092-52-6

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

potassium thioacetate
10387-40-3

potassium thioacetate

biotin
58-85-5

biotin

Conditions
ConditionsYield
In water at 0 - 60℃; Temperature;97%
5-((3aR,6S,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid

5-((3aR,6S,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With hydrogenchloride; sodium dithionite; water; sodium hydroxide In water at 55 - 90℃; for 0.5h; Reagent/catalyst;95.8%
(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid
33607-60-2

(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With boron tribromide In dichloromethane at -5 - 50℃; for 1.16667h; Inert atmosphere;
Stage #2: With hydrogenchloride In water Temperature; Solvent;
95%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;
92%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;
92%
(3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile
31099-31-7

(3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: (3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;
95%
With water; hydrogen bromide for 10h; Reflux; Inert atmosphere;80%
Multi-step reaction with 2 steps
1: aq. HBr / toluene / 40 h / Heating
2: 22 g / aq. NaOH / toluene; methoxybenzene / 6 h / 30 °C
View Scheme
5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 10h; pH=9-11;93%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

biotin
58-85-5

biotin

Conditions
ConditionsYield
With potassium hydroxide at 20℃; for 10h; pH=9-11; Reagent/catalyst;92%
(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

Diethyl carbonate
105-58-8

Diethyl carbonate

biotin
58-85-5

biotin

Conditions
ConditionsYield
With methanetrisulfonic acid at 170℃; under 3000.3 - 4500.45 Torr; Reagent/catalyst; Pressure; Temperature; Autoclave;91.67%
(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester
292151-19-0

(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;
90%
With sulfuric acid; water; acetic acid at 20 - 80℃;82%
With methanesulfonic acid In 1,3,5-trimethyl-benzene74%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester With hydrogen bromide for 48h; Substitution; Heating;
Stage #2: With sodium hydroxide; chloroformic acid ethyl ester Substitution;
Stage #3: With hydrogenchloride Hydrolysis;
benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate
179532-60-6

benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate With water; hydrogen bromide In xylene for 24h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; trichloromethyl chloroformate; pyrographite Product distribution / selectivity; more than 3 stages;
90%
Stage #1: benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; trichloromethyl chloroformate; pyrographite Product distribution / selectivity; more than 3 stages;
90%
C19H24N2O3S

C19H24N2O3S

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: C19H24N2O3S With palladium on activated charcoal; hydrogen In ethanol at 80 - 85℃; under 11400.8 - 15201 Torr; for 15h;
Stage #2: With sodium hydroxide In water at 25 - 30℃; for 5h; Solvent;
86.9%
<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-3-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester
83541-80-4

<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-3-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
With hydrogen bromide85%
With hydrogen bromide85%
<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester
151526-81-7

<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
With hydrogen bromide for 2h; Heating;85%
With hydrogen bromide for 2h; Heating;85%
Multi-step reaction with 2 steps
1.1: water; NaOH / methanol / 3 h / 40 °C
2.1: MeSO3H / xylene / 3 h / 135 °C
2.2: 3.06 g / water / 1 h / 10 °C
View Scheme
(3aS,6aR)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylidenepentanoic acid
324012-42-2

(3aS,6aR)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylidenepentanoic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With formic acid; methanesulfonic acid; palladium on activated charcoal for 15h; Catalytic hydrogenation; Debenzylation; Heating;85%
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / propan-2-ol / 18 h / 50 °C / 7500.6 Torr
2: 48percent HBr / 2 h / 100 °C
View Scheme
ethyl 5-iodopentanoate

ethyl 5-iodopentanoate

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione
28092-52-6

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: ethyl 5-iodopentanoate With bromine; zinc In tetrahydrofuran; toluene at 40℃; for 1h;
Stage #2: (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione With palladium 10% on activated carbon In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 28 - 40℃; for 5h; Further stages;
85%
(1-naphthyl)CH2CONH(CH2)2OPO2O-5\-d(GCGAGAAGTTAAGACCTATGCTCGC)-3\-O(CH2)3S-(4-succinimide-1)-(CH2)2O-(p-C6H4)COCH2(biotinate)

(1-naphthyl)CH2CONH(CH2)2OPO2O-5\-d(GCGAGAAGTTAAGACCTATGCTCGC)-3\-O(CH2)3S-(4-succinimide-1)-(CH2)2O-(p-C6H4)COCH2(biotinate)

biotin
58-85-5

biotin

Conditions
ConditionsYield
With 5'-d(CATAGGTCTTAACTT)-3'; sodium cacodylate In water; isopropyl alcohol at 20℃; pH=7.0; UV-irradiation;84%
N,N'-p-methoxybenzylbiotin
1245507-48-5

N,N'-p-methoxybenzylbiotin

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: N,N'-p-methoxybenzylbiotin With hydrogen bromide In toluene for 36h; Reflux;
Stage #2: With bis(trichloromethyl) carbonate; methoxybenzene In water for 2h; pH=10;
83%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide In water; toluene at -10 - -5℃;82.38%
biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: N,N'-dibenzylbiotin methyl ester With hydrogen bromide for 5h; Heating;
Stage #2: With sulfuric acid In methanol for 2h; Heating;
78%
With hydrogen bromide for 5h; Heating;0.041 g
phosgene
75-44-5

phosgene

(2S,3S,4R-3,4-diaminotetrahydrothiophen-2-yl)-pentanoate sodium

(2S,3S,4R-3,4-diaminotetrahydrothiophen-2-yl)-pentanoate sodium

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide In water; 1,2-dichloro-ethane at 70 - 80℃; for 4h; pH=10 - 12;75.8%
hept-6-ynoic acid
30964-00-2

hept-6-ynoic acid

amine-biotin

amine-biotin

isobutyl chloroformate
543-27-1

isobutyl chloroformate

A

alk-biotin

alk-biotin

B

biotin
58-85-5

biotin

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane; N,N-dimethyl-formamideA n/a
B 62%
phosgene
75-44-5

phosgene

(2S,3S,4R)-cis-5-(3,4-diaminotetrahydro-2-thienyl)valeric acid
22342-46-7

(2S,3S,4R)-cis-5-(3,4-diaminotetrahydro-2-thienyl)valeric acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With MANDELIC ACID
With (9S)-9-hydroxy-6'-methoxy-1-methyl-cinchonanium hydroxide
With L-arginine
5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid
76335-62-1

5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With ammonia; sodium; xylene
Stage #1: 5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid With methanesulfonic acid In xylene at 135℃; for 3h;
Stage #2: With water at 10℃; for 1h; Further stages.;
3.06 g
With ammonia; sodium; xylene
phosgene
75-44-5

phosgene

5-[3,4-bis-(2,2,2-trifluoro-acetylamino)-2,5-dihydro-thiophen-2-yl]-pentanoic acid methyl ester
64820-06-0

5-[3,4-bis-(2,2,2-trifluoro-acetylamino)-2,5-dihydro-thiophen-2-yl]-pentanoic acid methyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
(i) H2, Pd/C, (ii) K2CO3, H2O, (iii) /BRN= 1098367/; Multistep reaction;
[3-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-propyl]-malonic acid
57671-79-1

[3-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-propyl]-malonic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide at 180℃; for 0.5h;
5-((3aS)-1,3-diacetyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester
66244-06-2

5-((3aS)-1,3-diacetyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide In methanol; water
Sodium; 5-((3aR,6S,6aS)-1-benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoate

Sodium; 5-((3aR,6S,6aS)-1-benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoate

biotin
58-85-5

biotin

Conditions
ConditionsYield
With hydrogen bromide for 2h; Heating;
methanol
67-56-1

methanol

biotin
58-85-5

biotin

biotin methyl ester

biotin methyl ester

Conditions
ConditionsYield
With hydrogenchloride for 15h;100%
With sulfuric acid100%
Stage #1: methanol With acetyl chloride at 0℃; for 0.166667h;
Stage #2: biotin for 1h; Reflux;
100%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

biotin
58-85-5

biotin

biotin N-Hydroxysuccinimide ester
35013-72-0

biotin N-Hydroxysuccinimide ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;98%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;95%
ethanol
64-17-5

ethanol

biotin
58-85-5

biotin

5-[(3aS,4S,6aR)-2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl]-pentanoic acid ethyl ester
87573-52-2

5-[(3aS,4S,6aR)-2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl]-pentanoic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid100%
With sulfuric acid at 20℃;97%
With hydrogenchloride at 0 - 20℃; for 24h;91%
methyl 10-aminodecanoate hydrochloride
106590-42-5

methyl 10-aminodecanoate hydrochloride

biotin
58-85-5

biotin

10-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-decanoic acid methyl ester

10-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-decanoic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide100%
glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

biotin
58-85-5

biotin

[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-acetic acid methyl ester

[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-acetic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide100%
tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate
153086-78-3

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

biotin
58-85-5

biotin

tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate
175885-18-4

tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 17.5h; Inert atmosphere;100%
Stage #1: biotin With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate In dichloromethane at 20℃; for 16h;
96%
C2HF3O2*C6H14N4O2
929537-66-6

C2HF3O2*C6H14N4O2

biotin
58-85-5

biotin

N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide
945633-30-7

N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions
ConditionsYield
With 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetratetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide100%
C8H17NO5

C8H17NO5

biotin
58-85-5

biotin

C19H33N3O7S
1123762-87-7

C19H33N3O7S

Conditions
ConditionsYield
With 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetratetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide100%
1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-amine
1278996-71-6

1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-amine

biotin
58-85-5

biotin

1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-biotinylamide
1278996-72-7

1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-biotinylamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;100%
N,N-dimethylethylenediamine

N,N-dimethylethylenediamine

biotin
58-85-5

biotin

2-N-biotinyl-N,N-dimethylethan-1,2-diamine
1338832-53-3

2-N-biotinyl-N,N-dimethylethan-1,2-diamine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 24h;100%
biotin
58-85-5

biotin

C41H56N4O7S

C41H56N4O7S

Conditions
ConditionsYield
Stage #1: biotin With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 40℃; for 0.5h; Inert atmosphere;
Stage #2: 3-{2-[2-(3-{[Bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-propoxy)-ethoxy]-ethoxy}-propylamine With triethylamine In N,N-dimethyl-formamide Inert atmosphere;
100%
N-(4-(4-(4-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)piperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide

N-(4-(4-(4-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)piperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide

biotin
58-85-5

biotin

N-(4-(2,6-dimethyl-4-(4-((13-oxo-17-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-3,6,9-trioxa-12-azaheptadecyl)oxy)piperidin-1-yl)phenyl)thiazol-2-yl)isonicotinamide

N-(4-(2,6-dimethyl-4-(4-((13-oxo-17-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-3,6,9-trioxa-12-azaheptadecyl)oxy)piperidin-1-yl)phenyl)thiazol-2-yl)isonicotinamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃;100%
N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

biotin
58-85-5

biotin

N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide100%
3-butene-1-amine
2524-49-4

3-butene-1-amine

biotin
58-85-5

biotin

C14H23N3O2S

C14H23N3O2S

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;100%
N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

biotin
58-85-5

biotin

N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide100%
1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

biotin
58-85-5

biotin

N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide
65953-56-2

N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide

Conditions
ConditionsYield
Stage #1: biotin With di(succinimido) carbonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;
Stage #2: 1,6-Hexanediamine In N,N-dimethyl-formamide Inert atmosphere;
99%
C29H37N5O4
1071926-11-8

C29H37N5O4

biotin
58-85-5

biotin

C39H51N7O6S
1071926-14-1

C39H51N7O6S

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;99%
8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine

8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine

biotin
58-85-5

biotin

C28H35IN8O4S2
1418215-37-8

C28H35IN8O4S2

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication; Inert atmosphere;99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication;99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication;99%
ethylenediamine
107-15-3

ethylenediamine

biotin
58-85-5

biotin

N-(2-aminoethyl)-5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanamide

N-(2-aminoethyl)-5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanamide

Conditions
ConditionsYield
Stage #1: biotin With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 48 - 63℃; for 0.583333 - 0.666667h;
Stage #2: ethylenediamine In N,N-dimethyl-formamide for 72h;
99%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

biotin
58-85-5

biotin

biotin pentafluorophenyl ester
120550-35-8

biotin pentafluorophenyl ester

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide 0-5 deg C, 2.5 h; room temperature, 16 h;98%
With pyridine; dicyclohexyl-carbodiimide at 20 - 50℃;95%
With pyridine; 2`,3`-dideoxycytidine at 20℃; for 24h;93%
octanol
111-87-5

octanol

biotin
58-85-5

biotin

biotin octan-1-ol ester

biotin octan-1-ol ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 48h; Heating;98%
2-[2-(2-azidoethoxy)ethoxy]ethanol
86520-52-7

2-[2-(2-azidoethoxy)ethoxy]ethanol

biotin
58-85-5

biotin

C16H27N5O5S
1085938-08-4

C16H27N5O5S

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere;65%
acetyl chloride
75-36-5

acetyl chloride

biotin
58-85-5

biotin

biotin methyl ester
608-16-2

biotin methyl ester

Conditions
ConditionsYield
Stage #1: acetyl chloride In methanol at 0℃; for 0.25h;
Stage #2: biotin In methanol at 20℃; for 0.5h;
98%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Trp-OH
35737-15-6

Fmoc-Trp-OH

Fmoc-Lys-OH
105047-45-8

Fmoc-Lys-OH

Fmoc-D-Phe-OH
86123-10-6

Fmoc-D-Phe-OH

(9-fluorenylmethoxycarbonyl)-L-histidine
116611-64-4

(9-fluorenylmethoxycarbonyl)-L-histidine

biotin
58-85-5

biotin

C56H70N14O8S

C56H70N14O8S

Conditions
ConditionsYield
Stage #1: Fmoc-Lys-OH With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 4h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h;
Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Trp-OH; Fmoc-D-Phe-OH; (9-fluorenylmethoxycarbonyl)-L-histidine; biotin Further stages;
98%
N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2,4-dinitroaniline
929521-54-0

N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2,4-dinitroaniline

biotin
58-85-5

biotin

C22H32N6O8S

C22H32N6O8S

Conditions
ConditionsYield
Stage #1: biotin With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide
Stage #2: N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2,4-dinitroaniline In N,N-dimethyl-formamide for 0.166667h;
98%
4-azidoaniline
14860-64-1

4-azidoaniline

biotin
58-85-5

biotin

N-(4-azidophenyl)biotinamide

N-(4-azidophenyl)biotinamide

Conditions
ConditionsYield
Stage #1: biotin With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; Inert atmosphere;
Stage #2: 4-azidoaniline In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;
98%
bis(pentafluorophenyl)carbonate
59483-84-0

bis(pentafluorophenyl)carbonate

biotin
58-85-5

biotin

biotin pentafluorophenyl ester
120550-35-8

biotin pentafluorophenyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine In N,N-dimethyl-formamide for 2h;97%
biotin
58-85-5

biotin

5-((3aS,4S,6aR)-5-oxido-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid
23015-53-4

5-((3aS,4S,6aR)-5-oxido-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid

Conditions
ConditionsYield
With sodium peroxoborate tetrahydrate; acetic acid at 20℃; for 1.33333h;97%
With dihydrogen peroxide In acetic acid for 12h; Ambient temperature;
di-tert-butyl 4-<2-(tert-butoxycarbonyl)ethyl>-4-nitroheptanedicarboxylate
136587-00-3

di-tert-butyl 4-<2-(tert-butoxycarbonyl)ethyl>-4-nitroheptanedicarboxylate

biotin
58-85-5

biotin

Biotinamidotris[2-(tert-butoxycarbonyl)ethyl]methane
353737-53-8

Biotinamidotris[2-(tert-butoxycarbonyl)ethyl]methane

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 13h;97%

58-85-5Upstream product

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