N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester

Base Information

• Chemical Name: N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester
• CAS No.: 88818-14-8
• Molecular Formula: C₃₃H₃₇N₃O₉
• Molecular Weight: 619.671
• Mol file: 88818-14-8.mol

Synonyms:N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester

Chemical Property of N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester

There total 6 articles about N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester 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%

O-benzyl-N-<(3S,6S)-2-benzyloxycarbonyl-6-carboxy-6-<(chloroacetamido)methyl>perhydro-1,2-oxazine-3-carbonyl>-L-threonine benzyl ester (88818-12-6) → N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester (88818-14-8)

Guidance literature:

With thiourea; In ethanol; acetonitrile; at 40 ℃; for 48h;

DOI:10.1039/c39830001049

Reference yield:

(3S*,6S*)-2-benzyloxycarbonyl-6-<(chloroacetamido)methyl>-perhydro-1,2-oxazine-3,6-dicarboxylic acid (88818-10-4) → N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester (88818-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / acetonitrile / 0.5 h / 0 °C

2: 0 deg C, 1 h, 25 deg C, 10 min

3: 50 percent / thiourea / acetonitrile; ethanol / 48 h / 40 °C

With triethylamine; thiourea; In ethanol; acetonitrile;

DOI:10.1039/c39830001049

Reference yield:

C26H35ClN2O9 → N-<(3S,6S)-6-aminomethyl-2-benzyloxycarbonyl-6-carboxyperhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester (88818-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile / 1.) 0 deg C, 60 min; 2.) RT, 2 h

2: 41 percent / thiourea / acetonitrile; ethanol / 72 h / 40 °C

With triethylamine; thiourea; In ethanol; acetonitrile;

DOI:10.1016/S0040-4020(01)88799-8

upstream raw materials:

O-benzyl-N-<(3S,6S)-2-benzyloxycarbonyl-6-carboxy-6-<(chloroacetamido)methyl>perhydro-1,2-oxazine-3-carbonyl>-L-threonine benzyl ester

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

(3R,6R)-3-((1S,2R)-2-Benzyloxy-1-benzyloxycarbonyl-propylcarbamoyl)-6-[(2-chloro-acetylamino)-methyl]-[1,2]oxazinane-2,6-dicarboxylic acid 2-benzyl ester

N-<(3S,6S)-6-benzhydryloxycarbonyl-2-benzyloxycarbonyl-6-<(chloroacetamido)methyl>perhydro-1,2-oxazine-3-carbonyl>-O-benzyl-L-threonine benzyl ester

Downstream raw materials:

tabtoxin

O-benzyl-N-<(4S,7S)-6-benzyloxycarbonyl-1-oxo-5-oxa-2,6-diazaspiro<3.5>nonane-7-carbonyl>-L-threonine benzyl ester