35823-97-3

Basic information

• Product Name: methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-altropyranoside
• Synonyms: methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-altropyranoside
• CAS NO: 35823-97-3
• Molecular Weight: 386.401
• Mol File: 35823-97-3.mol
• Article Data: 41

Chemical Properties

• CAS DataBase Reference: methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-altropyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-altropyranoside(35823-97-3)
• EPA Substance Registry System: methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-altropyranoside(35823-97-3)

Safety Data

• Hazardous Substances Data: 35823-97-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 389-04-8 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 64-17-5 ethanol 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 93-97-0 benzoic acid anhydride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1202384-88-0 C₂₃H₂₄O₉ 
• 1372767-13-9 ethyl 2-deoxy-2-N-trichloroacetamido-3,4,6-tri-O-trimethylsilyl-1-thio-β-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 169557-88-4 ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamido)-1-thio-β-D-glucopyranoside 
• 635684-80-9 ethyl 2-deoxy-2-N-trichloroacetamido-1-thio-β-D-glucopyranoside 
• 473711-72-7 methyl 2,3-di-O-trimethylsilyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 198837-07-9 methyl-[O³-acetyl-O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranoside] 
• 169218-38-6 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-methanesulfonyl-α-D-glucopyranoside 
• 66674-14-4 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 33535-04-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 389-04-8 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 118246-07-4 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-D-rhamnopyranosyl)-β-D-glucopyranoside 
• 221002-70-6 methyl 2‐O‐benzoyl‐3‐O‐benzyl‐4,6‐O-benzylidene‐α‐D‐glucopyranoside 
• 118246-03-0 methyl 2,3,4-tri-O-acetyl-O-α-L-rhamnopyranosyI-(1->3)-2-O-benzoyl-4,6-O-benzylidene-O-α-D-gluco-pyranoside 
• 754224-34-5 Benzoic acid (2R,4aR,6R,7R,8R,8aR)-8-(2-chloro-acetoxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 945668-43-9 C₂₂H₂₁O₉SF₃ 
• 118204-02-7 methyl-2,3-dideoxy-2,3-ene-3-vinyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 118117-30-9 methyl-3-vinyl-4,6-O-benzylidene-α-D-allopyranoside 
• 118117-24-1 methyl-2,3-O-thionocarbonate-3-vinyl-4,6-O-benzylidene-α-D-allopyranoside 
• 118117-23-0 methyl-2-O-benzoyl-3-vinyl-4,6-O-benzylidene-α-D-allopyranoside 

Relevant articles and documents

Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols

Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-α-D-glucopyranoside and methyl 4,6-O-benzylidene- α-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination

DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate

The 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)-catalyzed regioselective acylation of carbohydrates and diols in ethyl acetate has been developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C. This method avoids metal catalysts and toxic solvents, which makes it comparatively green and mild, and it uses less organic base compared with other selective acylation methods. Mechanism studies indicated that DBN could catalyze the selective acylation of hydroxyl moieties through a dual H-bonding interaction.

Enhanced site-selectivity in acylation reactions with substrate-optimized catalysts on solid supports

A concept for site selective acylation of poly-hydroxylated substrates is presented where polymer-supported catalysts are employed: catalytically active DMAP units were combined with a library of small molecule peptides attached to the solid phase with the goal to identify substrate-optimized catalysts through library screening. For selected examples, we demonstrate how the optimized catalysts can convert “their” substrate with a markedly enhanced site-selectivity, compared to only DMAP. Due to the solid support, product purification is significantly simplified, and the peptidic catalysts can be easily reused in multiple cycles while conserving its efficiency.