(3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid

Base Information

• Chemical Name: (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid
• CAS No.: 108634-79-3
• Molecular Formula: C₁₇H₁₉NO₉
• Molecular Weight: 381.339

Synonyms:(3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid

Chemical Property of (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid

Chemical Property:

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Technology Process of (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid

There total 1 articles about (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

1-<(acetoxy)methyl>-3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene (108634-77-1) → (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid (108634-79-3)

Guidance literature:

With potassium permanganate; tetra(n-butyl)ammonium hydrogensulfate; In water; benzene; Ambient temperature;

DOI:10.1016/S0040-4020(01)87377-4

Reference yield: 4.9%

benzyl chloroformate (501-53-1,94274-21-2) + (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid (108634-79-3) → (3S*,6S*)-6-<(acetoxy)methyl>-2,3-bis(benzyloxycarbonyl)perhydro-1,2-oxazine-6-carboxylic acid (108634-80-6) + dibenzyl (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylate (108659-40-1)

Guidance literature:

With pyridine; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87377-4

Reference yield:

(3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylic acid (108634-79-3) + benzyl alcohol (100-51-6,185532-71-2) → (3S*,6S*)-6-<(acetoxy)methyl>-2,3-bis(benzyloxycarbonyl)perhydro-1,2-oxazine-6-carboxylic acid (108634-80-6) + dibenzyl (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylate (108659-40-1)

Guidance literature:

With p-toluenesulfonyl chloride; Product distribution; different amounts of reagent;

DOI:10.1016/S0040-4020(01)87377-4

upstream raw materials:

1-<(acetoxy)methyl>-3-benzyloxycarbonyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene

Downstream raw materials:

(3S*,6S*)-6-<(acetoxy)methyl>-2,3-bis(benzyloxycarbonyl)perhydro-1,2-oxazine-6-carboxylic acid

dibenzyl (3S*,6S*)-6-<(acetoxy)methyl>-2-benzyloxycarbonylperhydro-1,2-oxazine-3,6-dicarboxylate

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