86447-92-9

Basic information

• Product Name: methyl 4-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside
• Synonyms: methyl 4-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside
• CAS NO: 86447-92-9
• Molecular Weight: 308.375
• Mol File: 86447-92-9.mol

Chemical Properties

• CAS DataBase Reference: methyl 4-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside(86447-92-9)
• EPA Substance Registry System: methyl 4-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside(86447-92-9)

Safety Data

• Hazardous Substances Data: 86447-92-9(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-D-rhamnopyranoside 
• 112612-45-0 methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 148431-61-2 methyl 2-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside 
• 144872-94-6 methyl 4-O-benzyl-6-deoxy-2,3-di-O-(methylthio)thiocarbonyl-α-D-mannopyranoside 
• 73889-45-9 methyl 4-O-benzyl-2,3,6-trideoxy-α-D-erythro-hexopyranoside 
• 21317-50-0 methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside 
• 144993-44-2 methyl 4-O-benzyl-2,3,6-trideoxy-α-D-erythro-hex-2-enopyranoside 
• 152174-28-2 1,3-di-O-acetyl-2,4-di-O-benzyl-α-D-rhamnopyranose 
• 152174-34-0 ethyl 2-O-(3'-O-acetyl-2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside 
• 152174-29-3 ethyl 3,4-di-O-benzyl-2-O-(2',4'-di-O-benzyl-α-D-rhamnopyranosyl)-1-thio-α-D-rhamnopyranoside 
• 112612-48-3 3-O-acetyl-2,4-di-O-benzyl-α-D-rhamnopyranosyl chloride 
• 112612-46-1 methyl 2,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside 
• 128262-40-8 2-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-D-mannopyranosyl chloride 
• 134524-12-2 1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-D-mannopyranose 
• 134407-33-3 ethyl 3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside 
• 125519-98-4 methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside 

Relevant articles and documents

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Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor

1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose (11) was synthesised from thiophenyl α-d-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-α-d-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and subsequent protecting group manipulation gave d-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected d-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright

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The title compound (19), a conjugate of a trisaccharide based upon the repeating trisaccharide of α-D-rhamnose, which comprises the polysaccharide portion of 'A-band' lipopolysaccharide from a mutant (AK1401) of Pseudomonas aeruginosa, strain PAO1, with b

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New methods for the synthesis of tri- and di-deoxy sugar, namely methyl α-D-amicetoside, methyl α-D-perosaminoside and methyl α-D-janoside are described.The readily available methyl 6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside has been used as chiral