18929-79-8

Basic information

• Product Name: methyl 2,3,4-tri-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside
• Synonyms: methyl 2,3,4-tri-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside
• CAS NO: 18929-79-8
• Molecular Weight: 569.406
• Mol File: 18929-79-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside(18929-79-8)
• EPA Substance Registry System: methyl 2,3,4-tri-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside(18929-79-8)

Safety Data

• Hazardous Substances Data: 18929-79-8(Hazardous Substances Data)

Upstream product

• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 98-88-4 benzoyl chloride 
• 52290-43-4 methyl 6-deoxy-6-iodo-α-D-mannopyrannoside 
• 10364-94-0 1-benzoylimidazole 
• 52340-56-4 methyl 6-bromo-6-deoxy-α-D-mannopyranoside 
• 6340-63-2 methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-iodo-α-D-mannopyranoside 
• 67-56-1 methanol 

Downstream Products

• 95664-66-7 methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-lyxo-hex-5-enopyranoside 
• 95908-42-2 2L-2,5/3,4-2,3,4-tribenzoyloxy-5-hydroxycyclohexanone 

Relevant articles and documents

Nucleophilic displacement-reactions of the 4-sulfonyloxy group in derivatives having the D-manno configuration

Methyl 2,3-di-O-benzoyl-6-deoxy-4-O-(p-tolylsulfonyl) and 4-O--α-D-mannopyranosides (9 and 10) were prepared by three different routes from methyl α-D-mannopyranoside (1).The analogous 4-sulfonyloxy derivatives having HO-2 and HO-3 free (14 and 15) were also synthesized from 1.Nucleophilic substitution of the sulfonyloxy group of 9, 10, 14, and 15 by potassium thiocyanate in N,N-dimethylformamide was attempted.Compounds 9 and 10 gave a mixture of solvolysis products: methyl 2,3-di-O-benzoyl-6-deoxy-α-D-talopyranoside (17), methyl 3,4-di-O-benzoyl-6-deoxy-α-D-talopyranoside (18), and methyl 2,4-di-O-benzoyl-6-deoxy-α-D-talopyranoside (19), which are evidently formed by intramolecular displacement of the 4-sulfonate by backside attack of the C-2 benzoyloxy substituent, followed by benzoyl migration.The structure of compounds 17-19 was established by spectroscopic analysis, and then chemically confirmed.Although compound 14 decomposed during the substitution reaction, the 4-p-nitrophenylsulfonyl derivative 15 gave a 2:1 mixture of the 4-thiocyano derivatives with inversion and retention of the C-4 configuration.