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

Base Information

• Chemical Name: (3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<methyl>perhydro-1,2-oxazine-6-carboxylic acid
• CAS No.: 108634-84-0
• Molecular Formula: C₂₅H₂₇ClN₂O₉
• Molecular Weight: 534.95
• Mol file: 108634-84-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<methyl>perhydro-1,2-oxazine-6-carboxylic 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: 50.0%

benzyl chloroformate (501-53-1,94274-21-2) + (3S*,6S*)-benzyloxycarbonyl-6-<methyl>perhydro-1,2-oxazine-3,6-dicarboxylic acid (96657-51-1) → (3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<methyl>perhydro-1,2-oxazine-6-carboxylic acid (108634-84-0)

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

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

Reference yield: 91.0%

(3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<methyl>perhydro-1,2-oxazine-6-carboxylic acid (108634-84-0) → (3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<(methoxyamino)methyl>perhydro-1,2-oxazine-6-carboxylic acid (108634-85-1)

Guidance literature:

With thiourea; In ethanol; at 35 - 40 ℃;

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

Reference yield:

(3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<methyl>perhydro-1,2-oxazine-6-carboxylic acid (108634-84-0) → benzyl (4S*,7S*)-6-benzyloxycarbonyl-2-methoxy-1-oxo-5-oxa-2,6-diazaspiro<3.5>nonane-7-carboxylate (108634-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / thiourea / ethanol / 35 - 40 °C

2: 39 percent / KHCO₃, n-Bu₄NHSO₄, methanesulphonyl chloride / H₂O; CHCl₃ / Ambient temperature

With tetra(n-butyl)ammonium hydrogensulfate; potassium hydrogencarbonate; methanesulfonyl chloride; thiourea; In ethanol; chloroform; water;

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

upstream raw materials:

benzyl chloroformate

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

Downstream raw materials:

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

benzyl (4S*,7S*)-6-benzyloxycarbonyl-2-methoxy-1-oxo-5-oxa-2,6-diazaspiro<3.5>nonane-7-carboxylate