33639-75-7

Basic information

• Product Name: 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSE
• Synonyms: 6-DEOXY-2,3,4-TRI-O-BENZYL-L-GALACTOPYRANOSE;2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSE;2,3,4-TRI-O-BENZYL-ALPHA/BETA-L-FUCOSE;2,3,4-TRI-BZL-L-FUCOSE;TRI-O-BENZYL-L-FUCOPYRANOSE;2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSE, 99% MIN. HPLC
• CAS NO: 33639-75-7
• Molecular Formula: C₂₇H₃₀O₅
• Molecular Weight: 434.52
• Mol File: 33639-75-7.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSE(33639-75-7)
• EPA Substance Registry System: 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSE(33639-75-7)

Safety Data

• Hazardous Substances Data: 33639-75-7(Hazardous Substances Data)

Usage

Uses

An intermediate used for the preparation of selectin blockers and other oligosaccharides

Upstream product

• 250691-62-4 allyl 2,3,4-tri-O-benzyl-α-L-fucopyranoside 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 33639-74-6 (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 
• 242805-31-8 allyl 2,3,4-tri-O-benzyl-L-fucopyranoside 
• 139684-68-7 C₃₄H₃₆O₅ 
• 73-34-7 6-deoxy-L-galactose 
• 100-39-0 benzyl bromide 
• 242805-30-7 O-allyl-L-fucopyranose 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 

Downstream Products

• 134312-01-9 3,5-Dinitro-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyridine 
• 134311-74-3 3,5-Dinitro-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyridine 
• 177696-63-8 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl bromide 
• 144668-21-3 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one 
• 120703-61-9 1,6-anhydro-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranose 
• 120703-60-8 1,6-anhydro-3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranose 
• 120703-65-3 1,6-anhydro-3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-β-D-galactopyranose 
• 2079-46-1 (2R,3S,4S)-5,6-Bis-(phenyl-hydrazono)-hexane-2,3,4-triol 
• 64694-23-1 2,3,4-tri-O-benzyl-α-L-fucopyranosyl chloride 
• 1461750-25-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one 
• 103910-46-9 C₆₁H₆₄O₁₃P^(1-)*Na⁽¹⁺⁾ 
• 103866-96-2 Phosphorous acid 2-cyano-ethyl ester (2R,3R,4S,5S,6R)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester 
• 103866-97-3 Phosphoric acid 2-cyano-ethyl ester (2R,3R,4S,5S,6R)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester 
• 103866-99-5 Phosphoric acid 2-cyano-ethyl ester bis-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl) ester 

Relevant articles and documents

Synthesis method of Tilgliflozin intermediate

The invention belongs to the field of medicinal chemistry, and particularly relates to a synthesis method of a Tilgliflozin intermediate, which comprises the following steps: carrying out primary hydroxyl iodination and acetylation reaction on a compound A serving as a raw material to obtain iodinated acetate, reducing iodide into a methyl compound, preparing into a benzyl protection product, removing methyl protection, and reacting the swern oxidized hydroxyl in five steps to obtain a Tildagliflozin intermediate, namely a compound F. According to the method, the danger that in the prior art, due to the fact that selective silicon groups are adopted for protecting primary alcohol, benzyl is adopted for protecting three secondary alcohols, NaH is adopted, and consequently explosion is likely to happen is avoided, the reaction steps are further simplified, a high-yield final product can be obtained without column chromatography, and the total yield can reach 56%. The method provided by the invention is free of high-temperature and low-temperature reactions and dangerous reagents, the used raw materials are easy to obtain, the cost is greatly saved and is only 1/2-1/3 of that of a currently reported route, and the method has remarkable advantages.

Facile synthesis of sugar lactols via bromine-mediated oxidation of thioglycosides

Synthesis of a variety of sugar lactols (hemiacetals) has been accomplished in moderate to excellent yields by using bromine-mediated oxidation of thioglycosides. It was found that acetonitrile is the optimal solvent for this oxidation reaction. This approach involving bromine as oxidant is superior to that using N-bromosuccinimide (NBS) which produces byproduct succinimide often difficult to separate from the lactol products.