33019-03-3

Basic information

• Product Name: (R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE
• Synonyms: D-5-OXO-2-TETRAHYDROFURANCARBOXYLATE ETHYL (R-);(R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE;(-)-ethyl (R)-5-oxotetrahydrofuran-2-carboxylate;(R)-(?-Ethyl (R)-5-oxotetrahydro-2-furancarboxylate;(-)-Ethyl (R)-5-oxotetrahydro-2-furancarboxylate;(r)-(-)-γ-ethoxycarbonyl-γ-butyrolactone;ethoxycarbonyl-gamma-butyrolactone
• CAS NO: 33019-03-3
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• Mol File: 33019-03-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 151-155 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.163 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00312mmHg at 25°C
• Refractive Index: n20/D 1.448(lit.)
• CAS DataBase Reference: (R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE(33019-03-3)
• EPA Substance Registry System: (R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE(33019-03-3)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 33019-03-3(Hazardous Substances Data)

Usage

Description

(R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE is a chiral butyrolactone compound with a specific stereochemistry, characterized by the (R)-(-) prefix. It features a butyrolactone ring and an ethoxycarbonyl functional group, making it a versatile intermediate for organic synthesis and a valuable tool for organic chemists in developing new molecules.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE is used as a building block for the synthesis of pharmaceuticals and other organic compounds. Its unique structure allows it to participate in a wide range of chemical reactions, facilitating the development of new molecules with potential therapeutic applications.
Used in Organic Chemistry Research:
(R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE is used as a versatile intermediate in organic chemistry research for exploring various organic transformations. Its ability to engage in multiple chemical reactions makes it an essential component in the synthesis of complex organic molecules and the advancement of organic chemistry knowledge.

InChI:InChI=1/C7H10O4/c1-2-10-7(9)5-3-4-6(8)11-5/h5H,2-4H2,1H3/t5-/m1/s1

Upstream product

• 69134-53-8 (+/-)-diethyl 2-hydroxypentandioate 
• 5965-53-7 diethyl 2-ketoglutarate 
• 1126-51-8 (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester 
• 13095-48-2 L-hydroxyglutaric acid 
• 56-86-0 L-glutamic acid 
• 328-50-7 α-ketoglutaric acid 
• 141-78-6 ethyl acetate 
• 21461-85-8 (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 64-17-5 ethanol 
• 69556-79-2 (–)-(R)-diethyl 2-hydroxyglutarate 
• 53558-93-3 (R)-tetrahydro-5-oxo-2-furancarboxylic acid 

Downstream Products

• 147058-39-7 1-(2,3-dideoxy-beta-L-ribofuranosyl)-5-fluorocytosine 
• 1309671-47-3 C₅₁H₅₅N₂O₅P 
• 1309671-53-1 (S)-1-[bis(4-methoxyphenyl)phenylmethoxy]-5,5-di(pyren-1-yl)pentan-2-ol 
• 1309671-44-0 (S)-1-[bis(4-methoxyphenyl)phenylmethoxy]-5-(pyren-1-yl)pentan-2-ol 
• 1309671-51-9 (S)-1-(benzyloxy)-5,5-(dipyren-1-yl)pentan-2-ol 
• 1309671-49-5 (S)-5-(benzyloxy)-1,1-(dipyren-1-yl)pentan-1,4-diol 
• 1309671-42-8 (S)-1-(benzyloxy)-5-(pyren-1-yl)pentan-2-ol 
• 1309671-55-3 C₆₇H₆₃N₂O₅P 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 155768-47-1 -Ethyl 2-hydroxy-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate 
• 208173-52-8 (R)-5-Hydroxy-tetrahydro-furan-2-carboxylic acid ethyl ester 

Relevant articles and documents

Ring-opened 4-hydroxy-δ-valerolactone subunit as a key structural fragment of polyesters that degrade without acid formation

Random copolymers of ?-caprolactone with O-benzyl-protected 4-hydroxy- or 2,4-dihydroxy-δ-valerolactone after hydrogenation form γ-hydroxy functionalized polyesters that degrade via the cyclization to γ-butyrolactone fragments without carboxylic acid formation.

Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid

An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarate from 2-oxoglutaric acid. An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-γ- butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells.

Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo- 2-furancarboxylic acids and esters

Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned γ- lactones, by baker's yeast reduction of the corresponding ketodiesters was unsatisfactory. (C) 2000 Elsevier Science Ltd.