It acts as a glycosyl donor/activated sugar building block during the stepwise assembly of the pentasaccharide backbone. The molecule contains several protecting groups (benzyl, acetyl, and chloroformate) that control reactivity and stereochemistry during glycosylation, while the azido group serves as a precursor for an amine that is later converted to an N-sulfate group, an important structural feature required for the biological activity of Fondaparinux. The compound (2S,3S,4S,5R,6R)-methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3.2.1]octan-2-yloxy)-4,5-bis(benzyloxy)-3-(chlorocarbonyloxy)tetrahydro-2H-pyran-2-carboxylate is a protected carbohydrate intermediate used in the multistep synthesis of the anticoagulant drug Fondaparinux Sodium.
(2S,3S,4S,5R,6R)-methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3,2,1]octan-2-yloxy)-4,5-bis(benzyloxy)-3-(chlorocarbonyloxy)tetrahydro-2H-pyran-2-carboxylate
| API Name | Fondaparinux sodium |
|---|---|
| CAS No | 87907-02-6 |
| Molecular Formula | C30H32ClN3O12 |
| Molecular Weight | 662.0 g/mol |
| Synonyms | methyl (2S,3S,4S,5R,6R)-6-[[(1R,2S,3R,4R,5R)-3-acetyloxy-4-azido-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3-carbonochloridoyloxy-4,5-bis(phenylmethoxy -Show More |
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Frequently Asked Questions
It acts as a glycosyl donor/activated sugar building block during the stepwise assembly of the pentasaccharide backbone. The molecule contains several protecting groups (benzyl, acetyl, and chloroformate) that control reactivity and stereochemistry during glycosylation, while the azido group serves as a precursor for an amine that is later converted to an N-sulfate group, an important structural feature required for the biological activity of Fondaparinux. The compound (2S,3S,4S,5R,6R)-methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3.2.1]octan-2-yloxy)-4,5-bis(benzyloxy)-3-(chlorocarbonyloxy)tetrahydro-2H-pyran-2-carboxylate is a protected carbohydrate intermediate used in the multistep synthesis of the anticoagulant drug Fondaparinux Sodium.
The CAS number of (2S,3S,4S,5R,6R)-methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3,2,1]octan-2-yloxy)-4,5-bis(benzyloxy)-3-(chlorocarbonyloxy)tetrahydro-2H-pyran-2-carboxylate is 87907-02-6.
The molecular formula of (2S,3S,4S,5R,6R)-methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3,2,1]octan-2-yloxy)-4,5-bis(benzyloxy)-3-(chlorocarbonyloxy)tetrahydro-2H-pyran-2-carboxylate is C30H32ClN3O12.
The listed molecular weight of (2S,3S,4S,5R,6R)-methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3,2,1]octan-2-yloxy)-4,5-bis(benzyloxy)-3-(chlorocarbonyloxy)tetrahydro-2H-pyran-2-carboxylate is 662.0 g/mol.
(2S,3S,4S,5R,6R)-methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3,2,1]octan-2-yloxy)-4,5-bis(benzyloxy)-3-(chlorocarbonyloxy)tetrahydro-2H-pyran-2-carboxylate is listed as being used in connection with the following API: Fondaparinux sodium.
The listed synonym or IUPAC name for (2S,3S,4S,5R,6R)-methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3,2,1]octan-2-yloxy)-4,5-bis(benzyloxy)-3-(chlorocarbonyloxy)tetrahydro-2H-pyran-2-carboxylate is methyl (2S,3S,4S,5R,6R)-6-[[(1R,2S,3R,4R,5R)-3-acetyloxy-4-azido-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3-carbonochloridoyloxy-4,5-bis(phenylmethoxy -Show More.