86420-78-2

Basic information

• Product Name: methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside
• Synonyms: methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside
• CAS NO: 86420-78-2
• Molecular Weight: 264.278
• Mol File: 86420-78-2.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside(86420-78-2)
• EPA Substance Registry System: methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside(86420-78-2)

Safety Data

• Hazardous Substances Data: 86420-78-2(Hazardous Substances Data)

Upstream product

• 99265-93-7 methyl-[O⁴,O⁶-((R)-benzylidene)-O²,O³-bis-(toluene-4-sulfonyl)-α-D-altropyranoside] 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 28538-15-0 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-methanesulfonyl-α-D-altropyranoside] 
• 6748-86-3 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-p-toluenesulfonate 
• 71-43-2 benzene 
• 100-52-7 benzaldehyde 
• 3258-19-3 methyl-(2,3-anhydro-β-D-talopyranoside) 
• 86420-69-1 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2-O-p-toluenesulfonate 
• 86420-67-9 methyl 4,6-O-benzylidene-α-D-galactopyranoside 2-O-p-toluenesulfonate 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-altropyranoside 
• 6315-52-2 1,2-bis-tosyloxyethane 

Downstream Products

• 497180-22-0 methyl-[O⁴,O⁶-((R)-benzylidene)-3-iodo-3-deoxy-α-D-altropyranoside] 
• 626200-80-4 methyl 4,6-O-benzylidene-3-deoxy-3-C-ethyl-α-D-altropyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 71184-15-1 methyl-3-deoxyamino-4,6-dioxabenzylidene-α-D-altropyranose 
• 6198-74-9 methyl (R)-3-deoxy-α-D-arabinohexopyranose 
• 72904-78-0 methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside 
• 71117-41-4 methyl 4,6-O-benzylidene-α-D-altropyranoside 
• 30571-48-3 methyl-[O⁴,O⁶-((R)-benzylidene)-3-bromo-3-deoxy-α-D-altropyranoside] 
• 74410-53-0 Methyl 4,6-O-benzylidene-3-O-methyl-α-D-altropyranoside 
• 287191-51-9 methyl 4,6-O-benzylidene-β-D-idopyranoside 
• 129831-96-5 methyl 4,6-O-(S)-benzylidene-3-O-methyl-β-D-idopyranoside 
• 2484-81-3 methyl-[O²-acetyl-3-acetylamino-O⁴,O⁶-((S)-benzylidene)-3-deoxy-β-D-idopyranoside] 
• 74560-56-8 methyl 4,6-O-(S)-benzylidene-α-D-idopyranoside 
• 74560-63-7 methyl 4,6-O-(S)-benzylidene-3-methyl-α-D-idopyranoside 

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.

SUGAR-LINKER-DRUG CONJUGATES

The present disclosure relates to sugar-linker-drug conjugates, of the formula [A-B-]n-L-D, wherein A is a saccharide; B is a spacer, n is an integer selected from 1 to 3; L is a linker group and D is a drug having a chemically reactive functional group selected from the group consisting of a primary or secondary amine, hydroxyl, sulfhydryl, carboxyl, aldehyde and ketone. Pharmaceutical compositions comprising the conjugates and methods of using thern are also provided.

Evidence of cation-coordination involvement in directing the regioselective di-inversion reaction of vicinal di-sulfonate esters

Direct evidence has been obtained to confirm the unusual nucleophilic attack of an alkoxide at the S-center of sp3-hybridized sulfonyl esters. The unusual reaction pathway leads to S-O bond scission which is crucial for the regio- and stereoselective conversion of 2,3-di-O-sulfonates of 4,6-O-benzylidene-β-d-galactopyranosides into β-d-idopyranosides. In addition, strong evidence has been provided to clarify the role of the alkali counter-cation in the transformation. The cation is believed to influence the reaction rate via coordination to an oxygen in the sulfonate ester; the presence of a neighboring ring oxygen oriented in a cis-relationship greatly enhances reactivity of the sulfonyl ester.