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CAS 87907-35-5

benzyl ((2S,3R,4R,5S,6R)-4-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3-yl)carbamate

Codes: FOND-001

Application context (from source-drug indications)

Pulmonary embolismFondaparinux SodiumVenous thrombosisFondaparinux SodiumMyocardial infarctionFondaparinux SodiumAngina pectorisFondaparinux SodiumThromboembolismFondaparinux SodiumLiver diseaseFondaparinux Sodium

Source drugs (routes using this intermediate)

DrugTierExpiry
Fondaparinux SodiumTier C — Watch / trade-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

Fondaparinux SodiumOriginator routesteps: 10total yield: 166 mg
benzyl ((2S,3R,4R,5S,6R)-4-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3-yl)carbamate→((2R,3S,4R,5R,6S)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-3-hydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl acetate→methyl (5R,6S,7S)-7-(benzyloxy)-2-(tert-butoxy)-6-(2-chloroacetoxy)-2-methyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-5-carboxylate→methyl (2R,3S,4S,5R,6R)-5-acetoxy-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-3-(2-chloroacetoxy)tetrahydro-2H-pyran-2-carboxylate→methyl (2R,3S,4S,5R,6R)-5-acetoxy-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-3-hydroxytetrahydro-2H-pyran-2-carboxylate→methyl (2S,3S,4S,5R,6R)-6-(((2R,4R,5R,6R)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-bromotetrahydro-2H-pyran-3-yl)oxy)-4,5-bis(benzyloxy)-3-(2-chloroacetoxy)tetrahydro-2H-pyran-2-carboxylate→methyl (2R,3S,4S,5R,6R)-5-acetoxy-3-(((2R,3R,4R,6R)-4-acetoxy-6-(acetoxymethyl)-3-azido-5-(((2R,3R,4S,5S,6S)-3,4-bis(benzyloxy)-5-(2-chloroacetoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)tetrahydro-2H-pyran-2-carboxylate→methyl (2R,3S,4S,5R,6R)-5-acetoxy-3-(((2R,3R,4R,6R)-4-acetoxy-6-(acetoxymethyl)-3-azido-5-(((2R,3R,4S,5S,6S)-3,4-bis(benzyloxy)-5-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)tetrahydro-2H-pyran-2-carboxylate→((2R,3S,4R,5R,6R)-5-azido-3,4-bis(benzyloxy)-6-bromotetrahydro-2H-pyran-2-yl)methyl acetate→methyl (2R,3S,4S,5R,6R)-5-acetoxy-3-(((2R,3R,4R,6R)-4-acetoxy-6-(acetoxymethyl)-5-(((2R,3R,4S,5S,6S)-5-(((2R,3R,4R,5S,6R)-6-(acetoxymethyl)-3-azido-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)-3,4-bis(benzyloxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)oxy)-3-azidotetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)tetrahydro-2H-pyran-2-carboxylate→(2S,3S,4S,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-azido-4,5-bis(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,4R,5R,6R)-5-azido-6-(((2R,3S,4R,5R,6R)-4-(benzyloxy)-6-(((2R,3S,4R,5R,6S)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-2-carboxy-5-hydroxytetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-carboxylic acid→sodium (2S,3S,4S,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-azido-4,5-bis(benzyloxy)-6-((sulfonatooxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,4R,5R,6R)-5-azido-6-(((2R,3S,4S,5R,6R)-4-(benzyloxy)-6-(((2R,3S,4R,5R,6S)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxy-2-((sulfonatooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-2-carboxylato-5-(sulfonatooxy)tetrahydro-2H-pyran-3-yl)oxy)-4-(sulfonatooxy)-2-((sulfonatooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-carboxylate→sodium (2S,3S,4R,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-((sulfonatooxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,4R,5R,6R)-5-amino-6-(((2R,3S,4S,5R,6R)-6-(((2R,3S,4R,5R,6S)-5-amino-4-hydroxy-6-methoxy-2-((sulfonatooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-2-carboxylato-4-hydroxy-5-(sulfonatooxy)tetrahydro-2H-pyran-3-yl)oxy)-4-(sulfonatooxy)-2-((sulfonatooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-2-carboxylate

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