99541-22-7

Basic information

• Product Name: 1,6:2,3-Dianhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-beta-D-mannopyranose min. 99%
• Synonyms: 1,6:2,3-Dianhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-beta-D-mannopyranose min. 99%;1,6:2,3-Dianhydro-4-O-[2,3-bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-beta-D-glucopyranosyl]-beta-D-mannopyranose;-D-Mannopyranose, 1,6:2,3-dianhydro-4-O-[2,3-bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)--D-glucopyranosyl]-;1,6:2,3-Dianhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-b-D-glucopyranosyl)-b-D-mannopyranose
• CAS NO: 99541-22-7
• Molecular Formula: C₃₃H₃₄O₉
• Molecular Weight: 574.62
• Mol File: 99541-22-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,6:2,3-Dianhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-beta-D-mannopyranose min. 99%(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6:2,3-Dianhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-beta-D-mannopyranose min. 99%(99541-22-7)
• EPA Substance Registry System: 1,6:2,3-Dianhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-beta-D-mannopyranose min. 99%(99541-22-7)

Safety Data

• Hazardous Substances Data: 99541-22-7(Hazardous Substances Data)

Usage

Chemical structure

A complex carbohydrate with multiple benzyl groups attached to its glucopyranosyl and mannopyranose components.

Purity

At least 99%.

Application

Commonly used in synthetic organic chemistry as a building block for creating larger, more complex molecules.

Functional groups

Contains benzyl groups, benzylidene groups, and glycosidic linkages.

Stereochemistry

The compound has a beta-D-mannopyranose configuration.

Solubility

The solubility of 1,6:2,3-Dianhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-beta-D-mannopyranose min. 99% may vary depending on the solvent used, but it is generally soluble in organic solvents like methanol, ethanol, and dimethyl sulfoxide (DMSO).

Stability

The compound is stable under normal laboratory conditions, but should be stored in a cool, dry place and protected from light to maintain its purity and stability.

Safety

As with any chemical compound, appropriate safety precautions should be taken when handling this substance, including the use of gloves, eye protection, and a lab coat. Inhalation or ingestion should be avoided, and proper disposal methods should be followed.

Upstream product

• 150126-09-3 C₁₉H₂₂O₉ 
• 100-39-0 benzyl bromide 
• 135362-94-6 C₂₆H₃₀O₁₂S 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 35405-71-1 1,6-anhydro-β-D-cellobiose 
• 99571-46-7 2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose 

Downstream Products

• 99541-27-2 O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 100752-65-6 O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 100752-72-5 (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid 
• 99541-25-0 O-(2,3-di-O-benzyl-4-O-(chloroacetyl)-6-O-trityl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 100752-71-4 (2S,3S,4S,5R,6R)-6-((1R,2S,3R,4R,5R)-3-Acetoxy-4-azido-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid 
• 99541-23-8 O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 99541-26-1 O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 99541-24-9 O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 87907-02-6 O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 135415-93-9 (1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol 

Relevant articles and documents

AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM

The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.

Synthesis, from cellobiose, of a trisaccharide closely related to the GlcNAc----GlcA----GlcN segment of the antithrombin-binding sequence of heparin.

O-(2-Deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1----4)- O-(beta-D- glucopyranosyluronic acid)-(1----4)-1,6-anhydro-2-deoxy-2-sulfamido-6-O-sulfo-beta-D-gl ucopyranose pentasodium salt (14) was synthesized as a heparin-related oligosaccharide. The glycosyl acceptor (derived from cellobiose) and a glycosyl donor, 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide, were coupled in the presence of mercuric bromide and molecular sieves 4A to afford a 69% yield of fully protected trisaccharide, namely, O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1 ----4)- O-(methyl 2,3-di-O-benzyl-beta-D-glucopyranosyluronate)-(1----4)-3-O-acetyl- 1,6-anhydro-2 - azido-2-deoxy-beta-D-glucopyranose (10), which was converted into the partially sulfated trisaccharide 14. Compound 10 also underwent acetolysis to afford the glycosyl acetate, for further elongation of the glycosyl chain.