6936-66-9

Basic information

• Product Name: 5-(1,2-dihydroxyethyl)-3-hydroxy-oxolan-2-one
• Synonyms: 5-(1,2-dihydroxyethyl)-3-hydroxy-oxolan-2-one;3-Deoxy-D-xylo-hexonic acid 1,4-lactone;3-Deoxy-D-xylo-hexonic acid γ-lactone
• CAS NO: 6936-66-9
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 0
• Mol File: 6936-66-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 446.9°C at 760 mmHg
• Flash Point: 194.5°C
• Appearance: /
• Density: 1.561g/cm³
• Vapor Pressure: 7.27E-10mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 5-(1,2-dihydroxyethyl)-3-hydroxy-oxolan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1,2-dihydroxyethyl)-3-hydroxy-oxolan-2-one(6936-66-9)
• EPA Substance Registry System: 5-(1,2-dihydroxyethyl)-3-hydroxy-oxolan-2-one(6936-66-9)

Safety Data

• Hazardous Substances Data: 6936-66-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H10O5/c7-2-4(9)5-1-3(8)6(10)11-5/h3-5,7-9H,1-2H2

Upstream product

• 17510-99-5 4,5,6-trihydroxy-2-oxohexanoic acid 
• 61259-48-1 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone 

Downstream Products

• 284031-37-4 1,3,6-trideoxy-1,6-imino-D-xylo-hexitol 
• 2774-29-0 (3aR,5R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 22323-55-3 3-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose 

Relevant articles and documents

PROCESS FOR PRODUCING 2-DEOXYALDOSE COMPOUND

An object of the present invention is to provide a method for preparing 2-deoxyaldoses on industrial scale in which the yield or the volumetric efficiency is excellent and the operation is simple, as compared to the conventionally known preparation method.A compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by the catalytic hydrogenation method using a metal such as palladium or the like, or a compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by using a hydride reducing agent in a solvent of not more than 30 weight times the amount of the above compound, for synthesizing 2-keto-3-deoxyaldonic acid. The 2-keto-deoxyaldonic acid was decarboxylated to obtain 2-deoxyaldoses.The method of the present invention is economical and efficiently excellent.

Preparation of 3-Deoxy-aldonolactones by Hydrogenolysis of Acetylated Aldonolactones

Acetylated aldono-1,4-lactones, when treated with hydrogen in the presence of triethylamine and palladium on carbon, form acetylated 3-deoxy-aldono-1,4-lactones in high yield through elimination of the 3-acetoxy group and subsequent stereospecific hydrogenation of the unsaturated intermediate.Thus, acetylated D-galactono-1,4-lactone (1) yields tri-O-acetyl-3-deoxy-D-xylo-hexono-1,4-lactone (3a).Acetylated D-mannono- or D-glucono-1,4-lactone both give 3-deoxy-D-arabino-hexono-1,4-lactone (10a), whereas the four acetylated D-pentono-1,4-lactones (14-17) all afford di-O-acetyl-D-threo-pentono-1,4-lactone (18a).D-Gluconolactone can be converted into (R)-γ-caprolactone (27) on treatment with hydrogen bromide followed by a series of reductions.Similarly, D-lyxonolactone produces 2,3-dideoxy-D-glycero-pentono-1,4-lactone (29).