55682-48-9

Basic information

• Product Name: 1,6-Anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose
• Synonyms: 1,6-Anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose;β-D-Glucopyranose, 1,6-anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-
• CAS NO: 55682-48-9
• Molecular Formula: C₂₀H₂₁N₃O₄
• Molecular Weight: 367.403
• Mol File: 55682-48-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,6-Anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose(55682-48-9)
• EPA Substance Registry System: 1,6-Anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose(55682-48-9)

Safety Data

• Hazardous Substances Data: 55682-48-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
1,6-Anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose is used as a synthetic intermediate for the preparation of various glycosidic compounds, leveraging its unique structural features to facilitate the formation of complex carbohydrate derivatives.
Used in Medicinal Chemistry:
In the medicinal chemistry field, 1,6-Anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose is utilized as a key component in the development of bioactive molecules, potentially contributing to the creation of novel pharmaceutical agents with specific therapeutic properties.
Used in Material Science:
1,6-Anhydro-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose is also employed in material science as a precursor for the synthesis of new materials with unique properties, such as improved biocompatibility or specific binding affinities, which can be applied in various high-tech applications.

InChI:InChI=1/C20H21N3O4/c21-23-22-17-19(25-12-15-9-5-2-6-10-15)18(16-13-26-20(17)27-16)24-11-14-7-3-1-4-8-14/h1-10,16-20H,11-13H2/t16-,17-,18-,19-,20-/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 67546-20-7 1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 55682-47-8 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose 
• 97292-02-9 1,6-anhydro-3,4-di-O-benzyl-2-O-<(trifluoromethyl)sulfonyl>-β-D-mannopyranose 
• 81353-38-0 (trimethylsilylethynyl)tributyltin 
• 443915-94-4 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate 
• 139437-39-1 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose 
• 13265-84-4 D-glucal 
• 67227-89-8 1,6-anhydro-3,4-di-O-benzyl-β-D-mannopyranoside 
• 383193-45-1 (1R,2S,4S,5R,6R)-5-methylsulfonyloxy-3,7,9-trioxatricyclo[4.2.1.0^2,4]nonane 
• 16939-77-8 1,6:3,4-dianhydro-β-D-galactopyranose 
• 3868-05-1 1,6-anhydro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 
• 530-26-7 D-Mannose 

Downstream Products

• 55682-49-0 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose 
• 55682-50-3 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide 
• 87326-62-3 1,6-anhydro-2-azido-3-O-benzoyl-2-deoxy-β-D-glucopyranose 
• 55682-57-0 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 214756-90-8 1,6-anhydro-2-amino-2-deoxy-3,4-di-O-benzyl-β-D-glucopyranose 
• 136172-58-2 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose 
• 135362-96-8 O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate 
• 135362-95-7 O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 
• 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 
• 135415-92-8 O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate 
• 1374030-67-7 6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranose 
• 154970-28-2 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 
• 1433984-02-1 2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl azide 
• 1433984-04-3 2-azido-2-deoxy-3,4-di-O-benzyl-β-D-glucopyranosyl azide 

Relevant articles and documents

Preparation method of fondaparinux sodium monosaccharide intermediate

The invention discloses a preparation method of a fondaparinux sodium monosaccharide intermediate. The preparation method comprises the following steps: (1) in the presence of an acid-binding agent, carrying out esterification reaction on a compound as shown in a formula (I) and a substituent sulfonic anhydride and/or a substituent sulfonyl halogen to generate a compound as shown in a formula (II); (2) carrying out a ring opening reaction on the compound as shown in the formula (II) in an acidic condition to generate a compound as shown in a formula (III); (3) carrying out benzylation reactionon the compound as shown in the formula (III) and benzyl monohalide in an alkaline condition to generate a compound as shown in a formula (IV); and (4) carrying out an azido reaction on the compoundas shown in the formula (IV) and alkali metal azide salt to generate a compound as shown in a formula (V) and caring out inner ether ring opening and acetylation reaction on the compound as shown in the formula (V) in a mixed solution of acetic anhydride and trifluoroacetic acid to generate a compound as shown in a formula (VI). The method can be used for obtaining an ideal product yield, and theraw materials are cheap, easily available and relatively few in three wastes. The formulae are as shown in the description.

Oligosaccharide compound and its manufacture and its intermediate

The purpose of the present invention is to provide an oligosaccharide with high versatility that can produce a protected sulfate oligosaccharide that can become a manufacturing intermediate of polysulfated hyaluronic acid, and to provide a manufacturing method therefor and an intermediate thereof. Position 2 amino groups in glucosamine, galactosamine, and the like can react with saccharide receptors having an electron attracting group such as glucuronic acid and protected sulfate groups, by using a saccharide donor protected by a specific protective group.

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

Background: Derivatives of D-glucosamine and D-galactosamine represent an important family of the cell surface glycan components and their fluorinated analogs found use as metabolic inhibitors of complex glycan biosynthesis, or as probes for the study of protein-carbohydrate interactions. This work is focused on the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds towards selected cancer cells is determined. Results: Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2-azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was introduced and masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 ± 3 μM and 54 ± 5 μM, respectively). Conclusion: A complete series of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine is now accessible by 1,6-anhydrohexopyranose chemistry. Intermediate fluorinated 1,6-anhydro-2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly.

Total synthesis of anticoagulant pentasaccharide fondaparinux

The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy including a convergent [3+2] coupling approach, orthogonal protecting groups and various glycosyl donors. The new methods of glycosylation were also used for controlling the stereochemical configuration and improving the yield of the glycosylation. In addition, HPLC and NMR methods to monitor the process of total synthesis of fondaparinux were employed. This work provides a comprehensive elaboration for the synthesis and analysis of fondaparinux based on related literature, as well as abundant information for the synthesis of heparin-like oligosaccharides. A matter of protection! The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy. The process of total synthesis was monitored by HPLC and NMR. This work will contribute to continued improvement of the multistep production of fondaparinux and provide abundant information for the synthesis of heparin-like oligosaccharides.

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.

PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.

A process for the preparation of 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose

The invention relates to a process for the preparation of 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose, consisting of reaction of 1,6-anhydro-2-azido-2-deoxy-D-glucopyranose with benzyl bromide in a mixture of aromatic organic solvent and dipolar aprotic solvent and in the presence of a mixture of solid sodium hydroxide with solid potassium carbonate, phase transfer catalyst and tertiary alcohol. 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose is useful for preparation of 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose, a building block for synthesis of glucosamine oligosaccharides.

A process for the preparation of 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose

The invention relates to a process for the preparation of 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose, which process comprises reaction of 1,6-anhydro-2-azido-2-deoxy-D-glucopyranose with benzyl bromide in acetonitrile in the presence of solid sodium hydroxide to form 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose; subsequent reaction of 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose with acetic anhydride in the presence of trifluoroacetic acid to form 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose; and treatment of 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose with piperidine in THF. 6-0-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose is useful as a building block for synthesis of glucosamine oligosaccharides.

OLIGOSACCHARIDE COMPOUNDS FOR USE IN MOBILISING STEM CELLS

A compound of the following formula or a salt, solvate or formula (I) and a pharmaceutical composition containing said compound. It concerns also its use in the treatment of cancer and/or of pathological angiogenesis and/or in promoting the mobilisation of stem cells, in particular hematopoietic stem cells.

A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy

A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building bocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.