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

Base Information

• Chemical Name: (3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<<(tert-butoxycarbonyl)amino>methyl>perhydro-1,2-oxazine-6-carboxylic acid
• CAS No.: 102115-97-9
• Molecular Formula: C₂₇H₃₂N₂O₉
• Molecular Weight: 528.559
• Mol file: 102115-97-9.mol

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

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

There total 1 articles about (3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<<(tert-butoxycarbonyl)amino>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: 4.8%

benzyl chloroformate (501-53-1,94274-21-2) + (3S*,6S*)-2-benzyloxycarbonyl-6-<<(tert-butoxycarbonyl)amino>methyl>perhydro-1,2-oxazine-3,6-dicarboxylic acid (102115-96-8) → (3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<<(tert-butoxycarbonyl)amino>methyl>perhydro-1,2-oxazine-6-carboxylic acid (102115-97-9) + dibenzyl (3S*,6S*)-2-benzyloxycarbonyl-6-<<(tert-butoxycarbonyl)amino>methyl>perhydro-1,2-oxazine-3,6-dicarboxylate (108634-95-3)

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

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

Reference yield: 99.0%

(3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<<(tert-butoxycarbonyl)amino>methyl>perhydro-1,2-oxazine-6-carboxylic acid (102115-97-9) → (3S*,6S*)-6-<(amino)methyl>-2,3-bis(benzyloxycarbonyl)perhydro-1,2-oxazine-6-carboxylic acid (102115-98-0)

Guidance literature:

With formic acid; for 2h; Ambient temperature;

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

Reference yield:

(3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<<(tert-butoxycarbonyl)amino>methyl>perhydro-1,2-oxazine-6-carboxylic acid (102115-97-9) → (+/-)-tabtoxinine-β-lactam (65709-93-5,102209-37-0,137764-24-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / 98percent formic acid / 3 h / 25 °C

2: 63 percent / Ph₃P, di-2-pyridyl disulphide / acetonitrile / 2 h / 80 °C

3: 100 percent / H₂ / 10percent Pd/C / ethanol

With formic acid; 2,2'-dipyridyldisulphide; hydrogen; triphenylphosphine; palladium on activated charcoal; In ethanol; acetonitrile;

DOI:10.1039/c39850001549

upstream raw materials:

benzyl chloroformate

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

Downstream raw materials:

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

(+/-)-tabtoxinine-β-lactam

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