136172-58-2

Usage

Uses

Used in Organic Chemistry Research:
D-Glucopyranose, 2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-, 1,6-diacetate is used as a research compound for the development of new organic synthesis methods and the study of carbohydrate chemistry. Its unique structure allows for the exploration of novel reactions and the creation of advanced carbohydrate-based molecules.
Used in Bioorganic Chemistry:
In the field of bioorganic chemistry, D-Glucopyranose, 2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-, 1,6-diacetate is used as a key intermediate for the synthesis of biologically active molecules. Its azide group can be employed in click chemistry reactions, which are crucial for the rapid and efficient assembly of complex molecules.
Used in Pharmaceutical Industry:
D-Glucopyranose, 2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-, 1,6-diacetate is used as a building block for the development of pharmaceutical compounds, particularly those targeting carbohydrate-based drug discovery. Its unique functional groups enable the creation of novel drug candidates with potential therapeutic applications.
Used in Material Science:
In material science, D-Glucopyranose, 2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-, 1,6-diacetate is used as a component in the design of advanced materials with specific properties. Its ability to form complex structures makes it a valuable asset in the development of new materials with tailored characteristics for various applications.

Upstream product

• 100-39-0 benzyl bromide 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 3868-05-1 1,6-anhydro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 16939-77-8 1,6:3,4-dianhydro-β-D-galactopyranose 
• 383193-45-1 (1R,2S,4S,5R,6R)-5-methylsulfonyloxy-3,7,9-trioxatricyclo[4.2.1.0^2,4]nonane 
• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 
• 108-24-7 acetic anhydride 
• 95015-29-5 methyl-2-azido-3,4,5-tri-O-benzyl-2-desoxy-α-D-glucopyranoside 
• 55682-47-8 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose 
• 67546-20-7 1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 55682-48-9 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose 

Downstream Products

• 61135-01-1 6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose 
• 157896-03-2 6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose 
• 133076-40-1 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate 
• 157967-50-5 ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside 
• 55682-50-3 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide 
• 211238-74-3 C₆₂H₇₂N₂O₁₅S 
• 154918-98-6 methyl 2,4-di-O-benzyl-6-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside 

Relevant academic research and scientific papers

Preparation method of fondaparin sodium intermediate

The invention relates to a preparation method of a fondaparin sodium intermediate. In particular, the invention relates to a preparation method of a compound of formula 3, R1 is an alkyl protecting group or a hydroxy protecting group; and a process for preparation of fondaparin sodium from the compound of formula 3.

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.

PREPARATION OF MONOSACCHARIDES, DISACCHARIDES, TRISACCHARIDES, AND PENTASACCHARIDES OF HEPARINOIDS

The present invention provides preparations of monosaccharides, disaccharides, trisaccharides, and pentasaccharides of heparinoids. The present invention also provides novel monosaccharides, disaccharides, trisaccharides and pentasaccharides for use in th

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.

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.

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.

Synthesis of a Cell Wall Component of Haemophilus (Actinobacillus) Pleuropneumoniae Serotype 5

The disaccharide α-D-GlcNAcp-(1-5)-β-KDO-2-OCH2CH2CH2NH2 containing a spacer β-linked to KDO is prepared via iodonium ion-assisted glycosylation of a suitable KDO acceptor with ethyl 2-azido-2-deoxy-3,4-di-O-benzyl-1-thio-α/β-D-glucopyranoside.The key KDO building unit is synthesized in 7 steps starting with 2,3:5,6-di-O-isopropylidene-D-mannitol.

STEREOSPECIFIC SYNTHESIS OF PARTIALLY PROTECTED 2-AZIDO-2-DEOXY-D-GLUCOSYL D-MYO-INOSITOL: PRECURSOR OF A POTENTIAL INSULIN MIMETIC AND MEMBRANE PROTEIN ANCHORING SITE

Racemic and partially protected myo-inositol derivative 5 was coupled stereospecifically with the 2-azido-2-deoxy-glucosyl trichloroacetimidate donor 8.Optical resolution of the thus obtained diastereoisomeric mixture of dimers by silica gel column chromatography, and further protective group manipulations, afforded the suitably protected title compound 14.