(S)-(-)-alpha-Hydroxy-gamma-butyrolactone

Base Information

• Chemical Name: (S)-(-)-alpha-Hydroxy-gamma-butyrolactone
• CAS No.: 52079-23-9
• Molecular Formula: C4H6O3
• Molecular Weight: 102.09
• Hs Code.: 29322090
• Mol file: 52079-23-9.mol

Synonyms:2(3H)-Furanone,dihydro-3-hydroxy-, (S)-;(3S)-3-Hydroxydihydrofuran-2(3H)-one;(3S)-3-Hydroxytetrahydrofuran-2-one;(3S)-Dihydro-3-hydroxy-2(3H)furanone;2(3H)-Furanone,dihydro-3-hydroxy-, (3S)-;(S)-3-Hydroxydihydrofuran-2(3H)-one;(S)-a-Hydroxy-g-butyrolactone;L-a-Hydroxy-g-butyrolactone;

Chemical Property of (S)-(-)-alpha-Hydroxy-gamma-butyrolactone

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.00371mmHg at 25°C
• Refractive Index: n20/D 1.467(lit.)
• Boiling Point: 249.3 °C at 760 mmHg
• PKA: 13.07±0.20(Predicted)
• Flash Point: 122.1 °C
• PSA: 46.53000
• Density: 1.393 g/cm³
• LogP: -0.70580
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3S)-3-Hydroxydihydrofuran-2(3H)-one ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3S)-3-Hydroxydihydrofuran-2(3H)-one (cas# 52079-23-9) is a compound useful in organic synthesis. Used to prepare the polyether antibiotic monensin, functionalized D-ring side chains of vitamin D analogs, and pesticides.

Technology Process of (S)-(-)-alpha-Hydroxy-gamma-butyrolactone

There total 40 articles about (S)-(-)-alpha-Hydroxy-gamma-butyrolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(5S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one (124724-88-5) → (3S)-3-hydroxydihydrofuran-2(3H)-one (52079-23-9)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 25 ℃; for 1h;

DOI:10.1016/0957-4166(95)00371-1

Reference yield: 99.9%

(S)-Malic acid (97-67-6,78644-42-5) → (3S)-3-hydroxydihydrofuran-2(3H)-one (52079-23-9)

Guidance literature:

(S)-Malic acid; With trifluoroacetic anhydride; at 25 ℃; for 2h;

With methanol; for 12h;

With borane-THF; more than 3 stages;

Reference yield: 90.0%

2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid (113278-68-5,114458-03-6,119618-59-6,73991-95-4) → (3S)-3-hydroxydihydrofuran-2(3H)-one (52079-23-9)

Guidance literature:

2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid; With diborane; In tetrahydrofuran; Inert atmosphere;

With toluene-4-sulfonic acid; In benzene; Inert atmosphere;

DOI:10.1021/ol301495q

upstream raw materials:

(R)-2-Acetoxy-4-hydroxy-butyric acid ethyl ester

2-O-acetyl-3-deoxy-D-glycero-tetronolactone

3-hydroxy-2,5-dihydrofuran-2-one

α-acetonyl-γ-butyrolactone

Downstream raw materials:

(2R)-N-[2-(imidazol-4-yl)ethyl]-2,4-dihydroxybutyramide

(R)-α-N,N-diboc-aminoxy-γ-butyrolactone

(R)-α-benzyloxy-γ-butyrolactone

methyl (2R)-2-hydroxy-4-iodobutanoate

Refernces

• 1、 -. "CYCLIC PHOSPHATE SUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES". Page/Page column 47-48. . Retrieved 2018/04/11.
• 2、 Nakata, Kenya,Gotoh, Kouya,Ono, Keisuke,Futami, Kengo,Shiina, Isamu. "Kinetic resolution of racemic 2-hydroxy-γ-butyrolactones by asymmetric esterification using diphenylacetic acid with pivalic anhydride and a chiral acyl-transfer catalyst". supporting information. p. 1170 - 1173. Retrieved 2013/05/21.