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Cas Database

104227-71-6

104227-71-6

Identification

  • Product Name:Carbamic acid,[(3S)-tetrahydro-5-oxo-3-furanyl]-, 1,1-dimethylethyl ester (9CI)

  • CAS Number: 104227-71-6

  • EINECS:

  • Molecular Weight:201.222

  • Molecular Formula: C9H15NO4

  • HS Code:29321900

  • Mol File:104227-71-6.mol

Synonyms:Carbamicacid, (tetrahydro-5-oxo-3-furanyl)-, 1,1-dimethylethyl ester, (S)-;

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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

Supplier and reference price

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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:(S)-3-(Boc-Amino)-γ-butyrolactone
  • Packaging:5 g
  • Price:$ 435
  • Delivery:In stock
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:(S)-3-Boc-amino-gamma-butyrolactone 98%
  • Packaging:1g
  • Price:$ 84
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  • Manufacture/Brand:Crysdot
  • Product Description:(S)-tert-Butyl(5-oxotetrahydrofuran-3-yl)carbamate 97%
  • Packaging:25g
  • Price:$ 349
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  • Manufacture/Brand:Chemenu
  • Product Description:(S)-tert-Butyl(5-oxotetrahydrofuran-3-yl)carbamate 97%
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  • Manufacture/Brand:Chemenu
  • Product Description:(S)-tert-Butyl(5-oxotetrahydrofuran-3-yl)carbamate 97%
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Relevant articles and documentsAll total 15 Articles be found

Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis

Ueno, Masaharu,Huang, Yi-Yong,Yamano, Akihito,Kobayashi, Shu

, p. 2869 - 2871 (2013)

In response to Berke?'s report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed. Single crystals of HPA-12 for X-ray crystallographic analysis were obtained from ethyl propionate/n-hexane, and the stereochemistry was definitely determined to be 1R,3S, consistent with Berke?'s revised structure.

Highly Functionalized Organolithium Reagents for Enantiomerically Pure α-Amino Acid Synthesis

Kenworthy, Martin N.,Kilburn, John Paul,Taylor, Richard J. K.

, p. 19 - 22 (2004)

(Equation presented) Highly functionalized L-serine-derived organolithium reagents have been generated and reacted with a variety of electrophiles, delivering novel enantiomerically pure adducts. These adducts were then converted into homochiral amino alcohols and novel nonproteinogenic α-amino acids, including an aspartic acid mimic that has been synthesized in an enantiomerically pure form for the first time.

CRYSTALLINE FORMS OF A PYRROLIDONE DERIVATIVE USEFUL IN THE TREATMENT OF ALZHEIMER'S DISEASE AND PREPARATION THEREOF

-

Page/Page column 19, (2015/05/19)

The present invention provides processes to manufacture crystalline N-[(3S)-1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxo-pyrrolidin-3-yl]acetamide. Also disclosed are polymorphic forms of said compound as well as compounds useful as intermediates in the methods of the invention.

Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols

Xie, Xiaomin,Stahl, Shannon S.

supporting information, p. 3767 - 3770 (2015/04/14)

Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

Barfoot, Christopher W.,Harvey, Joanne E.,Kenworthy, Martin N.,Kilburn, John Paul,Ahmed, Mahmood,Taylor, Richard J.K.

, p. 3403 - 3417 (2007/10/03)

Homochiral, highly functionalised organolithium reagents derived from l-serine have been generated and reacted with electrophiles. The novel enantiomerically pure adducts thus obtained were then converted, through β-amino alcohols, into novel non-proteinogenic α-amino acids. The methodology also made available a novel boronic acid which was then employed as a Suzuki cross-coupling partner, elaborating a new pathway to phenylalanine analogues.

DIAMINE DERIVATIVES

-

Page/Page column 164-165, (2008/06/13)

A compound represented by formula (1):Q1-Q2-To-N(R1) -Q3-N(R2)-T1-Q4 [wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 represents the following group: (wherein Q5 is an alkylene group having 1 to 8 carbon atoms, or the like); and T0 and T1 are carbonyl groups or the like], a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after artificial valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

Process route upstream and downstream products

Process route

N-tert-butyloxycarbonylaspartic acid anhydride
91240-51-6,120409-48-5,30750-74-4

N-tert-butyloxycarbonylaspartic acid anhydride

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate
40856-59-5,132957-40-5

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 5 ℃; for 2h; Overall yield = 80 %; Overall yield = 36.5 g;
(S)-2-(tert-butoxycarbonylamino)-1,4-butanediol
128427-10-1,156627-42-8

(S)-2-(tert-butoxycarbonylamino)-1,4-butanediol

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate
40856-59-5,132957-40-5

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; In acetonitrile; at 22 ℃; for 6h; regioselective reaction;
71%
26%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl; In acetonitrile; at 22 ℃; for 2h; regioselective reaction;
33%
67%
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate
40856-59-5,132957-40-5

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / methanol / 3 h / 30 - 35 °C / pH 9.3-9.5
1.2: 25 - 35 °C
2.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 - 5 °C
With sodium tetrahydroborate; sodium hydroxide; In tetrahydrofuran; methanol;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate
87219-29-2

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In tetrahydrofuran;
85%
With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; for 24h;
palladium; In tetrahydrofuran;
With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; for 24h;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: AcCl
1.2: 100 percent / Et3N
2.1: 84 percent / Ph3P; hexachloroethane / CH2Cl2 / 2 h / 20 °C
3.1: 81 percent / LiBH4 / ethanol; tetrahydrofuran / 0 - 20 °C
4.1: 80 percent / Hunig's base / CH2Cl2 / 0 - 20 °C
5.1: HCl / methanol / 3 h / 20 °C
5.2: 65 percent Turnov. / CSA / benzene
With hydrogenchloride; lithium borohydride; hexachloroethane; N-ethyl-N,N-diisopropylamine; acetyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane;
With triethylamine; In dichloromethane;
3-(S)-tert-butoxycarbonylamino-4-(2-trimethylsilanyl-ethoxymethoxy)-butyric acid methyl ester
651036-65-6

3-(S)-tert-butoxycarbonylamino-4-(2-trimethylsilanyl-ethoxymethoxy)-butyric acid methyl ester

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
3-(S)-tert-butoxycarbonylamino-4-(2-trimethylsilanyl-ethoxymethoxy)-butyric acid methyl ester; With hydrogenchloride; In methanol; at 20 ℃; for 3h;
With camphor-10-sulfonic acid; In benzene; at 80 ℃;
50%
3-(S)-tert-butoxycarbonylamino-4-(2-trimethylsilanyl-ethoxymethoxy)-butyric acid methyl ester; With hydrogenchloride; In methanol; at 20 ℃; for 3h;
With camphor-10-sulfonic acid; In benzene;
65 % Turnov.
N-tert-butyloxycarbonylaspartic acid anhydride
91240-51-6,120409-48-5,30750-74-4

N-tert-butyloxycarbonylaspartic acid anhydride

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
With sodium tetrahydroborate; In tetrahydrofuran; for 2h;
76%
With sodium tetrahydroborate; Yield given. Multistep reaction; 1.) THF, -20 to 0 deg C, 2.) benzene, reflux ,3 h;
With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 16h;
(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
With camphor-10-sulfonic acid; In benzene; Heating;
97%
3-<i>tert</i>-butoxycarbonylamino-4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-thiobutyric acid <i>S</i>-ethyl ester
383418-08-4

3-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-thiobutyric acid S-ethyl ester

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

(R)-4-(tert-butyloxycarbonylamino)-γ-butyrolactone
137105-97-6

(R)-4-(tert-butyloxycarbonylamino)-γ-butyrolactone

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; Overall yield = 80 %;
80 % ee
2-(R)-tert-butoxycarbonylamino-3-chloro-propionic acid methyl ester
651035-84-6

2-(R)-tert-butoxycarbonylamino-3-chloro-propionic acid methyl ester

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester
104227-71-6

N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: 81 percent / LiBH4 / tetrahydrofuran; ethanol / 18 h / 20 °C
2.1: 95 percent / Hunig's base / CH2Cl2 / 18 h / 20 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
3.2: lithium naphthalenide / tetrahydrofuran; hexane / 2 h / -78 °C
3.3: tetrahydrofuran; hexane / -78 - -40 °C
4.1: 102 mg / diethyl ether; methanol; toluene / 0 °C
5.1: HCl / methanol / 3 h / 20 °C
5.2: 50 percent / CSA / benzene / 80 °C
With hydrogenchloride; lithium borohydride; n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; toluene;
Multi-step reaction with 4 steps
1.1: 81 percent / LiBH4 / ethanol; tetrahydrofuran / 0 - 20 °C
2.1: 80 percent / Hunig's base / CH2Cl2 / 0 - 20 °C
3.1: HCl / methanol / 3 h / 20 °C
3.2: 65 percent Turnov. / CSA / benzene
With hydrogenchloride; lithium borohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;

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