147514-07-6

Basic information

• Product Name: Methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• Synonyms: Methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS NO: 147514-07-6
• Molecular Weight: 476.526
• Mol File: 147514-07-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(147514-07-6)
• EPA Substance Registry System: Methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(147514-07-6)

Safety Data

• Hazardous Substances Data: 147514-07-6(Hazardous Substances Data)

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-39-0 benzyl bromide 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 76375-66-1 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 1319712-48-5 methyl 3-O-benzoyl-2,6-di-O-benzyl-α-D-glucopyranoside 
• 58341-66-5 methyl 2,6-di-O-benzyl-α-D-glucopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 147425-41-0 (4S,5R)-4-[(1S,2S,3R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-5-phenylsulfanylmethyl-hex-5-enyl]-3-(tert-butyl-dimethyl-silanyl)-5-methyl-oxazolidin-2-one 
• 158548-98-2 (4S,5R)-3-(tert-Butyl-dimethyl-silanyl)-4-{(S)-(tert-butyl-dimethyl-silanyloxy)-[(4S,5R)-2,2-dimethyl-5-(2-phenylsulfanylmethyl-allyl)-[1,3]dioxolan-4-yl]-methyl}-5-methyl-oxazolidin-2-one 
• 147425-42-1 (4S,5R)-3-(tert-Butyl-dimethyl-silanyl)-4-[(1S,2S,3R)-1-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-5-phenylsulfanylmethyl-hex-5-enyl]-5-methyl-oxazolidin-2-one 
• 147425-45-4 (1'R,2'S,3'R,4S,5R)-4-<5'-Oxo-2',3'-(2-propylidenedioxy)cyclohexyl>-5-methyl-3-<(4-methylphenyl)methanesulfonyl>-2-oxazolidinone 
• 158549-02-1 (1'R,2'S,3'R,4S,5R)-4-<5'-Methylidene-2',3'-(2-propylidenedioxy)cyclohexyl>-5-methyl-3-<(4-methylphenyl)methanesulfonyl>-2-oxazolidinone 

Relevant articles and documents

Synthesis of a series of maltotriose phosphates with an evaluation of the utility of a fluorous phosphate protecting group

A series of methyl maltotrioside phosphates were synthesized for application in the determination of the actual molecular substrate of the Lafora enzyme involved in Lafora disease. Several different synthetic routes were applied for the successful synthesis of six methyl maltotrioside phosphate regioisomers. The utility of a new fluorous phosphate protecting group was also evaluated, but its utility was found to be limited in this particular late stage introduction.

Synthesis of D-2-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate from D-glucose

A route to a novel, structurally modified D-myo-inositol 1,3,4,5-tetrakisphosphate analogue, D-2-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate 3, is described, involving as the key steps a selective protection of methyl α-D-glucopyranoside and subsequent catalytic Ferrier rearrangement to a deoxyinosose. Thus, methyl α-D-glucopyranoside was converted by an improved procedure into methyl 4,6-O-benzylidene-α-D-glucopyranoside 4 and thence into methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 7 without recourse to column chromatography. Compound 7 was converted into methyl 3,4-di-O-benzoyl-2-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 12 via methyl 3,4-di-O-benzoyl-2-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside 8. Rearrangement of enol ether 12 with mercury(II) trifluoroacetate provided (2S,3R,4S,5R)-2,3-dibenzoyloxy-4-benzyloxy-5-hydroxycyclohexanone 13 and (2S,3A,4S,5S)-2,3-dibenzoyloxy-4-benzyloxy-5-hydroxycyclohexanone 14. Attempts to invert the configuration at position 5 of compound 14 were unsuccessful, but provided a number of discrete products. Reduction of compound 13 and saponification furnished L-1-O-benzyl-3-deoxy-scyll-inositol 23, which was phosphorylated and deprotected to give the target 3.

The diastereoselective synthesis of (+)-actinobolin from D-glucose

The carbocyclic ring of actinobolin was constructed by a [3 + 3] annulation of a D-galactosamine derivative with 3-phenylthio-2-(trimethylsilylmethyl)propene. Formation of the lactone and acylation with L-alanine according to literature precedent gave (+)