99541-26-1

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (2S,3S,4S,5S,6S)-6-[(1S,2S,3S,4R,5R)-3-(acetyloxy)-4-azido-6,8-dioxabicyclo[3.2.1]oct-2-yl]Methyl-4 is used as a pharmaceutical candidate for its potential therapeutic properties. Methyl (2S,3S,4S,5S,6S)-6-[(1S,2S,3S,4R,5R)-3-( acetyloxy)-4-azido-6,8-dioxabicyclo[3.2.1]oct-2-yl]Methyl-4's unique structure and functional groups may contribute to its ability to interact with biological targets, making it a promising candidate for the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, Methyl (2S,3S,4S,5S,6S)-6-[(1S,2S,3S,4R,5R)-3-(acetyloxy)-4-azido-6,8-dioxabicyclo[3.2.1]oct-2-yl]Methyl-4 can be utilized as a building block or intermediate in the synthesis of more complex molecules. Its versatile structure and functional groups provide opportunities for further chemical modifications and the creation of novel compounds with specific properties.
Used in Material Science:
Methyl (2S,3S,4S,5S,6S)-6-[(1S,2S,3S,4R,5R)-3-(acetyloxy)-4-azido-6,8-dioxabicyclo[3.2.1]oct-2-yl]Methyl-4 may also find applications in material science, where its unique structure and properties can be harnessed to develop new materials with specific characteristics. For example, it could be used in the design of polymers, coatings, or other materials with tailored properties for various industrial applications.
Used in Research and Development:
Due to its complex structure and potential for various applications, Methyl (2S,3S,4S,5S,6S)-6-[(1S,2S,3S,4R,5R)-3-(acetyloxy)-4-azido-6,8-dioxabicyclo[3.2.1]oct-2-yl]Methyl-4 is a valuable compound for research and development purposes. It can be used as a subject of study to explore its chemical and biological properties, as well as its potential applications in various fields, including pharmaceuticals, material science, and chemical synthesis.

Upstream product

• 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 
• 186581-53-3 diazomethane 
• 74-88-4 methyl iodide 
• 145773-08-6 allyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 20746-64-9 allyl (R)-4,6-O-benzylidene-β-D-gluco-pyranoside 
• 2595-07-5 allyl β-D-glucopyranoside 
• 492-61-5 β-D-glucose 
• 596087-18-2 4-methylphenyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 67546-20-7 1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 87907-01-5 methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosyl bromide)uronate 
• 1610791-09-7 C₃₀H₃₁ClO₇S 
• 1352561-81-9 C₂₈H₃₀O₆S 
• 850416-39-6 p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside 

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 
• 100752-72-5 (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 
• 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 
• 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 

Relevant academic research and scientific papers

Preparation method of fondaparinux sodium disaccharide intermediate

The invention discloses a preparation method of fondaparinux sodium disaccharide intermediate. 1-O-substituent sulfonyl-2,3-bis-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranose directly reacts with 1,6-dehydrated-2-deoxy-2-azido-3-O-acetyl-beta-D-glucopyranose to prepare the fondaparinux sodium disaccharide intermediate as shown in a formula I; and meanwhile, the fondaparinux sodium intermediate asshown in the formula I can be used as a raw material to synthesize fondaparinux sodium intermediate as shown in a formula IV. The preparation method is simple and small in steps, the yield is high, the atomic utilization rate is high, the three wastes are small, and the preparation method is suitable for industrial large-scale production. Please see the description for the formula.

Novel technology for preparing disaccharide fragment of fondaparinux sodium intermediate

The invention relates to a novel technology for preparing disaccharide fragment of an anticoagulant drug fondaparinux sodium intermediate. The technology has the advantages of short reaction route, high efficiency, and easy purifying of the intermediate, and is suitable for commercial production of the full protection heparin pentasaccharide.

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.

PROCESS FOR THE PREPARATION OF DISACCHARIDES APPLIED TO HEPARIN PENTASACCHARIDES

The invention provides an intermediate of formula (I) and the process for making the same. This intermediate is useful in the process for making polysaccharides, and more particularly fondaparinux.

A facile preparation of uronates via selective oxidation with TEMPO/KBr/Ca(OCl)2 under aqueous conditions

Addition of solid Ca(OCl)2 as the terminal oxidant in the TEMPO-mediated selective oxidation has the benefit of easier operation. A variety of partially protected saccharide derivatives (1a-l) have been successfully converted into the corresponding uronate derivatives, including disaccharide building blocks for GAG fragments and precursors to saponins. The beneficial effect of Aliquat 336 was also disclosed in the oxidation of certain substrates.

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.