89615-39-4

Basic information

• Product Name: benzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• Synonyms: benzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• CAS NO: 89615-39-4
• Molecular Weight: 630.781
• Mol File: 89615-39-4.mol
• Article Data: 26

Chemical Properties

• CAS DataBase Reference: benzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside(89615-39-4)
• EPA Substance Registry System: benzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside(89615-39-4)

Safety Data

• Hazardous Substances Data: 89615-39-4(Hazardous Substances Data)

Upstream product

• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 100-44-7 benzyl chloride 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 1927-62-4 tetrahydro-2-(benzyloxy)-2H-pyran 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 100-51-6 benzyl alcohol 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 1370590-24-1 2-allylphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 1370590-22-9 2-allylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 83-87-4 D-Mannose pentaacetate 
• 881198-66-9 2-allyloxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 530-26-7 D-Mannose 

Downstream Products

• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 79522-92-2 Benzyl-6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosid 
• 35094-65-6 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 4356-77-8 acetyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 85339-00-0 benzyl-6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 27851-30-5 benzyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-gluco-pyranoside 
• 61277-58-5 ((2R,3R,4S,5R)-3,4,5,6-tetraki s(benzyloxy)tetrahydro-2H-pyran-2-yl)methanol 
• 1393113-98-8 C₃₈H₄₀O₉ 
• 176040-72-5 benzyl O-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1[*]6)-O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1[*]6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 176040-69-0 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-(1[*]6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 176040-70-3 benzyl 6-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 176200-10-5 benzyl 2,3,4-tri-O-benzyl-6-O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 

Relevant articles and documents

Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor

Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.

N-benzoylglycine/thiourea cooperative catalyzed stereoselective O-glycosidation: Activation of O-glycosyl trichloroacetimidate donors

A new practical utility for β-stereoselective glycosylation via activation of O-glycosyl trichloroacetimidate donors using N-benzoylglycine/thiourea cooperative catalysis has been demonstrated. This method represents the first instance where amino acid derived N-benzoylglycine is used as a catalyst for O–glycosylation under mild reaction conditions at ambient temperature. NMR spectroscopy studies suggest that thiourea cocatalyst exhibit a cooperative behaviour that has a strong effect on the reaction rate, yield, and the β-selectivity.

Metal-free and VOC-free: O -glycosylation in supercritical CO2

Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylation reactions in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology described here can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to temperature changes than to pressure modification, with glycosyl chlorides requiring higher temperatures to be activated than glycosyl bromides. Pivaloyl groups act as good CO2-philic units and are shown to be the best choice to obtain good stereoselectivities. The relevance of the fluid nature and supercritical conditions was also evidenced.