334834-19-4

Basic information

• Product Name: 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside
• Synonyms: 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside
• CAS NO: 334834-19-4
• Molecular Weight: 356.375
• Mol File: 334834-19-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside(334834-19-4)
• EPA Substance Registry System: 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside(334834-19-4)

Safety Data

• Hazardous Substances Data: 334834-19-4(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 5531-09-9 3-O-benzyl-L-idopyranose 
• 37776-17-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 37776-15-1 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 134198-40-6 6-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-glucofuranose 
• 334834-37-6 1,6-anhydro-2,3,4-triO-trimethylsilyl-β-L-idopyranose 
• 60619-47-8 1,6-anhydro-β-L-idopyranose 
• 87357-54-8 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose 
• 81562-09-6 6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside 
• 882689-03-4 Benzoic acid (S)-2-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester 
• 98-88-4 benzoyl chloride 

Downstream Products

• 657395-02-3 6-O-acetyl-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate 
• 657395-03-4 C₅₅H₅₁Cl₃N₄O₁₃ 
• 657395-07-8 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate 
• 657395-06-7 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl levulinate 
• 657395-04-5 C₇₄H₇₂N₆O₁₈ 
• 1314746-21-8 1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose 
• 1415973-62-4 1,6-anhydro-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 

Relevant articles and documents

Synthesis of Fondaparinux: Modular synthesis investigation for heparin synthesis

The anti-thromboembolic pentasaccharide Fondaparinux was synthesized in 36 steps for the longest linear route, with 0.017% overall yield from d-glucose. Only three kinds of protecting groups were used for hydroxyl protection, Bn, Ac, and Bz, to accomplish this complex synthesis without decreasing the synthetic efficiency. Three l-idopyranosyl donors were investigated. Thioethyl glycoside is an efficient donor for l-idopyranosyl glycosylation with full α-selectivity, while l-idopyranosyl trichloroacetimidate resulted in poor α/β selectivity. A practical synthesis of key intermediate 1,6-anhydro-l-idopyranose 17 by H+/β-CD catalyst was developed.

METHODS AND INTERMEDIATES FOR THE PREPARATION OF FONDAPARINUX

The present invention relates to methods for the synthesis of fondaparinux and intermediates thereto.

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