65556-00-5

Basic information

• Product Name: methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside
• Synonyms: methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside
• CAS NO: 65556-00-5
• Molecular Weight: 590.672
• Mol File: 65556-00-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside(65556-00-5)
• EPA Substance Registry System: methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside(65556-00-5)

Safety Data

• Hazardous Substances Data: 65556-00-5(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 50-99-7 D-glucose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 28538-12-7 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 
• 6698-34-6 methyl 4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 

Downstream Products

• 66674-15-5 methyl 4,6-O-benzylidene-3-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 6972-98-1 methyl-[O⁴,O⁶-((R)-ethylidene)-O²,O³-bis-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 86420-78-2 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside 
• 102219-87-4 methyl 4-O-<(S)-cyanophenylmethyl>-2,3-di-O-tosyl-α-D-glucopyranoside 
• 102243-10-7 methyl 6-O-<(R)-cyanophenylmethyl>-2,3-di-O-tosyl-α-D-glucopyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 120123-51-5 methyl 6-O-benzoyl-2,3-di-O-tosyl-α-D-glucopyranoside 
• 56607-37-5 methyl 4-O-benzoyl-2,3-di-O-tosyl-α-D-glucopyranoside 
• 130272-53-6 methyl 4,6-O-benzylidene-2,3-dideoxy-β-D-threo-hex-2-enoside 
• 65530-28-1 methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside 
• 1352406-78-0 methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside 
• 1352406-79-1 methyl 2-O-(p-methoxybenzyl)-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside 
• 1352406-80-4 methyl 4-O-benzyl-3-deoxy-α-D-gluco-hexodialdo-1,5-pyranoside 

Relevant articles and documents

A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α-d-glucopyranoside was developed by a domino epoxide ring opening- xanthate migration to afford 1,3-oxathiolane-2-thiones in high yields. The stereochemical outcome of the new C–S bond was defined by the configuration of the starting materials. The 1,3-oxathiolane-2-thiones were subsequently submitted to a second tandem reaction affording the corresponding 2,3-episulfide alcohols. The thiosugars obtained are useful building blocks for the synthesis of thiooligosaccharides with potential biological properties.

α- and β-Lipomycin: Total syntheses by sequential stille couplings and assignment of the absolute configuration of all stereogenic centers

40 years ago spectroscopy, derivatization, and degradation revealed the structures of α-lipomycin and its aglycon β-lipomycin except for the configurations of their side-chain stereocenters. We synthesized all relevant β-lipomycin candidates: the (12R,13S

A scalable approach to obtaining orthogonally protected β-d-idopyranosides

A practical method to obtain orthogonally protected d-idopyranose from d-galactose has been developed, which is the first method to enable synthesis of the challenging β-d-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared d-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various β-idopyranose-containing oligosaccharide targets to further probe their biological functions.