73159-22-5

Upstream product

• 108-24-7 acetic anhydride 
• 35775-02-1 methyl 4,6-O-benzylidene-2-chloro-2-deoxy-α-D-mannopyranoside 
• 73159-21-4 methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 2-chlorosulphate 
• 88410-54-2 methyl 3-O-benzoyl-4,6-O-benzylidene-2-chloro-2-deoxy-α-D-mannopyranoside 
• 33535-04-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 18031-57-7 methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 

Relevant academic research and scientific papers

Halogenation reactions of derivatives of D-glucose and sucrose.

Treatment of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (1) with triphenylphophine-carbon tetrachloride-pyridine (reagent A) gave methyl 4,6-O-benzylidene-2-chloro-2-deoxy-alpha-D-mannopyranoside (2). When reagent A was used in excess, a further elimination reaction occurred to give methyl 4,6-O-benzylidene-2-chloro- (6, 60%) and -3-chloro-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside (7, 16%). Treatment of 1 with triphenylphosphine-carbon tetrabromide-pyridine (reagent B) caused little or no elimination, and 47% of methyl 4,6-O-benzylidene-2-bromo-2-deoxy-alpha-D-mannopyranoside (14) was obtained. On treatment with reagent A, methyl alpha-D-glucopyranoside (16) gave exclusively methyl 2,4,6-trichloro- 2,3,4,6-tetradeoxy-alpha-D-erythro-hex-2-enopyranoside (17), and methyl 4,6-O-benzylidene-beta-D-glucopyranoside (19) gave methyl 4,6-O-benzylidene-3-chloro-3-deoxy-beta-D-allopyranoside (20, 70%). However, with reagent B, 19 gave methyl 4,6-O-benzylidene-3-bromo-3-deoxy-beta-D-glucopyranoside (23, 66%), probably by way of double inversion of configuration at C-3. Likewise, with reagent A, methyl beta-D-glucopyranoside (25) gave methyl 2,4,6-trichloro- (26) and3,4,6-trichloro-2,3,4,-6-tetradeoxy- beta-D-threo-hex-2-enopyranoside (27), and 4,6-O-isopropylidenesucrose (28) gave mainly 3-chloro-3-deoxy-4,6-O-isopropylidene-alpha-D-allopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-beta-D-lyxo-hexulofuranoside (29) together with 3-chloro-3-deoxy-4,6-O-isopropylidene-alpha-D-allopyranosyl 1,4,6-trichloro-1,4,6-trideoxy-beta-D-fructofuranoside (30). The assignment of structure to 29 is tentative.

Method of preparation of 2-chloro-2-deoxysaccharides

A process for the preparation of a 2-chloro-2-deoxy-mono-, di- or oligo-saccharide comprises reaction of a mono-, di- or oligo-saccharide derivative having a free hydroxy group in at least 2- position and having the hydroxy group in at least the 1- and 3-

THE FIRST REPLACEMENT OF A CHLOROSUPHONYLOXY GROUP BY CHLORINE AT C-2 IN METHYL α-D-GLUCOPYRANOSIDE AND SUCROSE DERIVATIVES

Treatment of methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 2-chlorosulphate (2), 3,4,6,3',4',6'-hexa-O-acetylsucrose 2,1'-bis(chlorosulphate), 3,4,6,3',4',6'-hexa-O-acetyl-1'-O-benzoylsucrose 2-chlorosulphate, and 3,4,3',4'-tetra-O-acetyl-6,6'-d