79580-60-2

Basic information

• Product Name: (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone
• Synonyms: (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone
• CAS NO: 79580-60-2
• Molecular Weight: 274.227
• Mol File: 79580-60-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone(79580-60-2)
• EPA Substance Registry System: (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone(79580-60-2)

Safety Data

• Hazardous Substances Data: 79580-60-2(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 15384-37-9 D-xylono-1,4-lactone 
• 5461-96-1 ammonium D-xylonate 
• 64-19-7 acetic acid 
• 87-72-9 D-Xylose 
• 82796-87-0 D-xylono-1,5-lactone 

Downstream Products

• 26532-13-8 methyl 2,5-di-O-benzoyl-3-deoxy-α-D-threo-pentofuranoside 
• 219133-17-2 (2'S,5S)-2,2-dimethyl-5-<3'-(diphenyl-t-butylsilyloxy)-2'-tolylsulfonyloxy>-1,3-dioxane 
• 219313-77-6 (S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-2-ol 
• 162889-26-1 1α-di<(2-methoxyethoxy)methoxy>vitamin D₃ 
• 162889-21-6 (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-dihydro-furan-2-one 
• 166450-62-0 (2S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-2-(2-methoxy-ethoxymethoxy)-pentanal 
• 102717-31-7 (2S,4S)-5-(t-butyldiphenylsiloxy)-2-hydroxypentan-4-olide 
• 41294-56-8 1α-hydroxyvitamin D3 

Relevant articles and documents

A General Synthetic Route to A-Ring Hydroxylated Vitamin D Analogs from Pentoses

The enyne needed for coupling to a CD-ring fragment, namely, 3S,5R-oct-1-en-7-yne-3,5-diol, in the Trost-Dumas carbopalladation route to 1α,25-dihydroxyvitamin D3 was synthesized from D-xylose in 13 steps and 21percent yield.

Synthesis of two novel chiral building blocks for anti- And syn-1,3-diols

Two novel chiral building blocks 1 and 2 for anti- and syn-1,3-diols have been synthesized starting from the readily available and inexpensive D-(+)-xylose.

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).