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Cas Database

85026-59-1

85026-59-1

Identification

  • Product Name:1,2-Cyclopentanediol, 3-amino-5-(hydroxymethyl)-, (1R,2S,3R,5R)-

  • CAS Number: 85026-59-1

  • EINECS:

  • Molecular Weight:147.174

  • Molecular Formula: C6H13NO3

  • HS Code:

  • Mol File:85026-59-1.mol

Synonyms:(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol;3-amino-5-hydroxymethyl-cyclopentane-1,2-diol;(4a-carba-β-D-ribofuranosyl)amine;(1R,2S,3R,5R)-3-amino-5-hydroxymethylcyclopentane-1,2-diol;(1R,2S,3R,5R)-3-amino-5-hydroxymethyl-cyclopentane-1,2-diol;(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)-1-aminocyclopentane;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 14 Articles be found

Synthesis of 4a-Carba-d-lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α-Mannosidases

Zaji?ková, Mária,Monco?, Ján,?esták, Sergej,Kóňa, Juraj,Koó?, Miroslav,Bella, Maro?

, p. 1114 - 1124 (2019/01/24)

A synthetic approach to 4a-carba-d-lyxofuranose derivatives starting from d-lyxose is described. The protected 4a-carba-β-d-lyxofuranose was employed as the key intermediate for the synthesis of 4a-carba-d-lyxofuranose derivatives including novel 1-amino-1-deoxy-4a-carba-d-lyxofuranoses. Synthesized 4a-carba-d-lyxofuranoses were evaluated as inhibitors of GH38 α-mannosidases, namely, the Golgi (GMIIb) and lysosomal (LManII) α-mannosidases from Drosophila melanogaster and commercial Jack bean α-mannosidase (JBMan) from Canavalia ensiformis. The biochemical evaluation revealed that only 1-amino-1-deoxy-4a-carba-β-d-lyxofuranose exhibited reasonable inhibitory activity against GMIIb (IC50 = 200 μm). In addition, the results of biological evaluation were discussed by means of molecular modelling.

Stable NAD/NADH derivatives

-

, (2017/01/17)

The present invention provides for stable nicotinamide adenine dinucleotide (NAD/NADH) and nicotinamide adenine dinucleotide phosphate (NADP/NADPH) derivatives of formula (I), enzyme complexes of these derivatives and their use in biochemical detection methods and reagent kits.

Synthesis of carba-NAD and the structures of its ternary complexes with SIRT3 and SIRT5

Szczepankiewicz, Bruce G.,Dai, Han,Koppetsch, Karsten J.,Qian, Dongming,Jiang, Fan,Mao, Cheney,Perni, Robert B.

, p. 7319 - 7329 (2012/11/13)

Carba-NAD is a synthetic compound identical to NAD except for one substitution, where an oxygen atom adjacent to the anomeric linkage bearing nicotinamide is replaced with a methylene group. Because it is inert in nicotinamide displacement reactions, carba-NAD is an unreactive substrate analogue for NAD-consuming enzymes. SIRT3 and SIRT5 are NAD-consuming enzymes that are potential therapeutic targets for the treatment of metabolic diseases and cancers. We report an improved carba-NAD synthesis, including a pyrophosphate coupling method that proceeds in approximately 60% yield. We also disclose the X-ray crystal structures of the ternary complexes of SIRT3 and SIRT5 bound to a peptide substrate and carba-NAD. These X-ray crystal structures provide critical snapshots of the mechanism by which human sirtuins function as protein deacylation catalysts.

METHOD AND SUBSTANCES FOR PREPARATION OF N-SUBSTITUTED PYRIDINIUM COMPOUNDS

-

Page/Page column 10, (2011/02/24)

The present invention relates to a method for the synthesis of N-substituted carboxylated pyridinium compounds by reacting a pentamethine precursor with a primary amine. In this reaction an N-substituted alkoxycarbonyl pyridinium heterocycle is formed.

Variable strategy toward carbasugars and relatives. 4. Viable access to (4a-carbapentofuranosyl)amines, (5a-carbahexopyranosyl)amines, and amino acids thereof

Rassu, Gloria,Auzzas, Luciana,Pinna, Luigi,Zambrano, Vincenzo,Zanardi, Franca,Battistini, Lucia,Marzocchi, Lucia,Acquotti, Domenico,Casiraghi, Giovanni

, p. 5338 - 5342 (2007/10/03)

A chiral, divergent synthesis of two carbafuranosylamines, 1 and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)-oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields.

Process route upstream and downstream products

Process route

(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride
79200-57-0

(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
With potassium hydroxide; In ethanol; at 20 ℃; for 0.25h;
(-)-(1R,2R,3S,4R)-4-(N-tert-butyloxycarbonyl)amino-2,3-dimethylmethylenedioxy-1-(hydroxymethyl)cyclopentane
183505-22-8

(-)-(1R,2R,3S,4R)-4-(N-tert-butyloxycarbonyl)amino-2,3-dimethylmethylenedioxy-1-(hydroxymethyl)cyclopentane

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
With trifluoroacetic acid; In water; at 20 ℃; for 6h;
5.2g
(1R,2S,3R,4R)-[2,3-bis-(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-cyclopentyl]carbamic acid tert-butyl ester
445469-23-8

(1R,2S,3R,4R)-[2,3-bis-(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-cyclopentyl]carbamic acid tert-butyl ester

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
(1R,2S,3R,4R)-[2,3-bis-(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-cyclopentyl]carbamic acid tert-butyl ester; With hydrogenchloride; In tetrahydrofuran; methanol; water; at 20 ℃; for 6h;
With DOWEX (H+ form); Further stages.;
99%
(1R,2S,3R,5R)-3-Azido-5-hydroxymethyl-cyclopentane-1,2-diol
76910-19-5

(1R,2S,3R,5R)-3-Azido-5-hydroxymethyl-cyclopentane-1,2-diol

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
With hydrogen; nickel; In methanol; Yield given;
With hydrogen; nickel; In methanol; for 0.5h; under 760 Torr; Yield given;
((1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentyl)-carbamic acid benzyl ester
189823-70-9

((1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentyl)-carbamic acid benzyl ester

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
With sodium; In tetrahydrofuran; methanol; ammonia; at -78 ℃; for 2h;
61%
(3aR,4R,6R,6aS)-2,2-dimethyl-6-(trityloxymethyl)tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

(3aR,4R,6R,6aS)-2,2-dimethyl-6-(trityloxymethyl)tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

Conditions
Conditions Yield
With hydrogenchloride; In methanol; water; at 0 - 50 ℃;
82%
(3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol
112543-75-6

(3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
Multi-step reaction with 11 steps
1: imidazole / dimethylformamide / Ambient temperature
2: PCC, molecular sieves / CH2Cl2 / 4 h / Ambient temperature
3: 80 percent / sodium borohydride / methanol / 1 h / 0 °C
5: acetic acid / H2O; methanol / 87 h / Ambient temperature
6: camphorsulfonic acid / dimethylformamide / 3 h
7: 95 percent / pyridine / 1 h / 0 °C
8: 90 percent / sodium azide / dimethylformamide / 9 h / 120 - 140 °C
9: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature
10: 80percent aq. acetic acid / 2 h / 60 °C
11: H2 / Raney nickel / methanol / 0.5 h / 760 Torr
With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; acetic acid; pyridinium chlorochromate; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
Multi-step reaction with 11 steps
1: imidazole / dimethylformamide / Ambient temperature
2: PCC, molecular sieves / CH2Cl2 / 4 h / Ambient temperature
3: 1.) silica gel, 2.) sodium borohydride / 1.) CH2Cl2, RT, 2.5 h, 2.) methanol, 0 deg C, 1 h
5: acetic acid / H2O; methanol / 87 h / Ambient temperature
6: camphorsulfonic acid / dimethylformamide / 3 h
7: 95 percent / pyridine / 1 h / 0 °C
8: 90 percent / sodium azide / dimethylformamide / 9 h / 120 - 140 °C
9: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature
10: 80percent aq. acetic acid / 2 h / 60 °C
11: H2 / Raney nickel / methanol / 0.5 h / 760 Torr
With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; silica gel; acetic acid; pyridinium chlorochromate; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
Multi-step reaction with 10 steps
1: imidazole / dimethylformamide / Ambient temperature
2: PCC, molecular sieves / CH2Cl2 / 4 h / Ambient temperature
3: 1.) silica gel, 2.) sodium borohydride / 1.) CH2Cl2, RT, 2.5 h, 2.) methanol, 0 deg C, 1 h
4: acetic acid / H2O; methanol / 87 h / Ambient temperature
5: camphorsulfonic acid / dimethylformamide / 3 h
6: 95 percent / pyridine / 1 h / 0 °C
7: 90 percent / sodium azide / dimethylformamide / 9 h / 120 - 140 °C
8: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature
9: 80percent aq. acetic acid / 2 h / 60 °C
10: H2 / Raney nickel / methanol / 0.5 h / 760 Torr
With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; silica gel; acetic acid; pyridinium chlorochromate; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
(-)-(1R,2R,3S,4R)-4-azido-1-(hydroxymethyl)-2,3-(isopropylidenedioxy)cyclopentane
113180-72-6

(-)-(1R,2R,3S,4R)-4-azido-1-(hydroxymethyl)-2,3-(isopropylidenedioxy)cyclopentane

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 80percent aq. acetic acid / 2 h / 60 °C
2: H2 / Raney nickel / methanol / 0.5 h / 760 Torr
With hydrogen; acetic acid; nickel; In methanol;
Multi-step reaction with 2 steps
1: 80percent AcOH / 60 °C
2: H2 / Raney Ni / methanol
With hydrogen; acetic acid; nickel; In methanol;
(1S,2S,3S,4S)-2-acetoxy-1-(acetoxymethyl)-3,4-(isopropylidenedioxy)cyclopentane
105285-29-8

(1S,2S,3S,4S)-2-acetoxy-1-(acetoxymethyl)-3,4-(isopropylidenedioxy)cyclopentane

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
Multi-step reaction with 12 steps
1: sodium methoxide / methanol / 0 °C
2: imidazole / dimethylformamide / Ambient temperature
3: PCC, molecular sieves / CH2Cl2 / 4 h / Ambient temperature
4: 80 percent / sodium borohydride / methanol / 1 h / 0 °C
6: acetic acid / H2O; methanol / 87 h / Ambient temperature
7: camphorsulfonic acid / dimethylformamide / 3 h
8: 95 percent / pyridine / 1 h / 0 °C
9: 90 percent / sodium azide / dimethylformamide / 9 h / 120 - 140 °C
10: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature
11: 80percent aq. acetic acid / 2 h / 60 °C
12: H2 / Raney nickel / methanol / 0.5 h / 760 Torr
With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; acetic acid; pyridinium chlorochromate; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
Multi-step reaction with 12 steps
1: sodium methoxide / methanol / 0 °C
2: imidazole / dimethylformamide / Ambient temperature
3: PCC, molecular sieves / CH2Cl2 / 4 h / Ambient temperature
4: 1.) silica gel, 2.) sodium borohydride / 1.) CH2Cl2, RT, 2.5 h, 2.) methanol, 0 deg C, 1 h
6: acetic acid / H2O; methanol / 87 h / Ambient temperature
7: camphorsulfonic acid / dimethylformamide / 3 h
8: 95 percent / pyridine / 1 h / 0 °C
9: 90 percent / sodium azide / dimethylformamide / 9 h / 120 - 140 °C
10: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature
11: 80percent aq. acetic acid / 2 h / 60 °C
12: H2 / Raney nickel / methanol / 0.5 h / 760 Torr
With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; silica gel; acetic acid; pyridinium chlorochromate; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
Multi-step reaction with 11 steps
1: sodium methoxide / methanol / 0 °C
2: imidazole / dimethylformamide / Ambient temperature
3: PCC, molecular sieves / CH2Cl2 / 4 h / Ambient temperature
4: 1.) silica gel, 2.) sodium borohydride / 1.) CH2Cl2, RT, 2.5 h, 2.) methanol, 0 deg C, 1 h
5: acetic acid / H2O; methanol / 87 h / Ambient temperature
6: camphorsulfonic acid / dimethylformamide / 3 h
7: 95 percent / pyridine / 1 h / 0 °C
8: 90 percent / sodium azide / dimethylformamide / 9 h / 120 - 140 °C
9: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature
10: 80percent aq. acetic acid / 2 h / 60 °C
11: H2 / Raney nickel / methanol / 0.5 h / 760 Torr
With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; silica gel; acetic acid; pyridinium chlorochromate; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
(1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-4-hydroxy-2,3-(isopropylidenedioxy)cyclopentane
112543-76-7

(1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-4-hydroxy-2,3-(isopropylidenedioxy)cyclopentane

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
85026-59-1,305384-32-1,780705-82-0

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 95 percent / pyridine / 1 h / 0 °C
2: 90 percent / sodium azide / dimethylformamide / 9 h / 120 - 140 °C
3: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature
4: 80percent aq. acetic acid / 2 h / 60 °C
5: H2 / Raney nickel / methanol / 0.5 h / 760 Torr
With pyridine; sodium azide; tetrabutyl ammonium fluoride; hydrogen; acetic acid; nickel; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps
1: 95 percent / pyridine
2: 90 percent / NaN3 / dimethylformamide / 120 - 140 °C
3: n-Bu4NF / tetrahydrofuran
4: 80percent AcOH / 60 °C
5: H2 / Raney Ni / methanol
With sodium azide; tetrabutyl ammonium fluoride; hydrogen; acetic acid; nickel; In tetrahydrofuran; pyridine; methanol; N,N-dimethyl-formamide;

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