17184-28-0

Basic information

• Product Name: Methyl 3,6-anhydro-α-D-glucofuranoside
• Synonyms: 1-O-Methyl-3,6-anhydro-α-D-glucofuranose;Methyl 3,6-anhydro-α-D-glucofuranoside
• CAS NO: 17184-28-0
• Molecular Formula: C₇H₁₂O₅
• Molecular Weight: 176.16718
• Mol File: 17184-28-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 3,6-anhydro-α-D-glucofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3,6-anhydro-α-D-glucofuranoside(17184-28-0)
• EPA Substance Registry System: Methyl 3,6-anhydro-α-D-glucofuranoside(17184-28-0)

Safety Data

• Hazardous Substances Data: 17184-28-0(Hazardous Substances Data)

Upstream product

• 13407-60-8 methyl-3,6-anhydro-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 7625-23-2 3,6-anhydro-D-glucose 
• 67-56-1 methanol 
• 2280-44-6 D-Glucose 
• 87638-78-6 3,6-anhydro-D-glucofuranose 
• 87595-96-8 Methyl-3,6-anhydro-2,5-di-O-tosyl-α-D-glucofuranosid 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 67-66-3 chloroform 
• 13421-89-1 methyl-[O⁴-(3,6-anhydro-β-D-glucopyranosyl)-3,6-anhydro-β-D-glucopyranoside] 
• 13421-89-1 methyl-[O⁴-(3,6-anhydro-α-D-glucopyranosyl)-3,6-anhydro-β-D-glucopyranoside] 
• 23661-33-8 methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 87638-77-5 Methyl-3,6-anhydro-β-D-glucofuranosid 

Downstream Products

• 7625-23-2 3,6-anhydro-D-glucose 
• 86883-39-8 Methyl-3,6-anhydro-5-O-tosyl-α-D-glucofuranosid 
• 87595-96-8 Methyl-3,6-anhydro-2,5-di-O-tosyl-α-D-glucofuranosid 
• 176850-42-3 4-Oxo-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-6-hydroxy-2-methoxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 176850-48-9 4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-6-hydroxy-2-methoxy-hexahydro-furo[3,2-b]furan-3-yl ester 

Relevant articles and documents

Acyloxonium ions in the high-yielding synthesis of oxolanes from alditols, hexoses, and hexonolactones catalysed by carboxylic acids in anhydrous hydrogen fluoride

Treatment of D-glucono-1,5- or D-mannono-1,4-lactone with anhydrous hydrogen fluoride catalysed by formic or acetic acid yields 3,6-anhydro-D-glucono- and -D-mannono-1,4-lactone, respectively.Similarly, D-mannitol is converted into 1,4-anhydro-D-mannitol and subsequently into the 1,4:3,6-dianhydride, whereas D-glucitol forms exclusively the 3,6-anhydride and, on further reaction, 1,4:3,6-dianhydro-D-glucitol.D-Glucose and 2-acetamido-2-deoxy-D-glucose are also converted into the corresponding 3,6-anhydrides by reaction with hydrogen fluoride and formic acid.13C-N.m.r. spectroscopy indicates that the reactions involve intermediate dioxolanyium ions.

Methyl 2,5:3,6-Dianhydro-D-mannofuranosides

Monotosylation of methyl 3,6-anhydro-β-D-glucofuranoside gives as minor reaction product 1 which yields by treatment with sodium ethanolate methyl 2,5:3,6-dianhydro-β-D-mannofuranoside (2).The α-anomer 6 is equally prepared from 3 which is obtained by selective monotosylation of methyl 3,6-anhydro-β-L-gulofuranoside.Reaction of methyl 3,6-anhydro-2,5-di-O-tosyl-α-D-glucofuranoside (5) gives only small amounts of 6 accompanied by the monotosylate 4.Mass and NMR spectra (2D-1H and 13C) of the new dianhydrides 2 and 6 are described.