(5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid benzyl ester

Base Information

• Chemical Name: (5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid benzyl ester
• CAS No.: 141698-12-6
• Molecular Formula: C₂₆H₃₆N₄O₇S₂
• Molecular Weight: 580.726

Synonyms:(5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid benzyl ester

Chemical Property of (5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid benzyl ester

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Technology Process of (5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid benzyl ester

There total 7 articles about (5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid 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: 90.0%

Boc-3-Me-Cys(Trt)-Pro-Gly-Cys(Acm)-OBzl (141698-11-5) → (5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid benzyl ester (141698-12-6)

Guidance literature:

With iodine; In methanol; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.65.2227

Reference yield:

H-Cys(Acm)-OBzl hydrochloride (79396-92-2) → (5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid benzyl ester (141698-12-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / triethylamine (TEA) / dimethylformamide / Ambient temperature

2: 98 percent / 1.4 M HCl / acetic acid / 0.33 h / Ambient temperature

3: 1.) N-hydroxysuccinimide (HOSu), dicyclohexylcarbodiimide (DCC), 2.) triethylamine (TEA) / 1.) THF, RT, 2 h, 2.) DMF, RT, overnight

4: 90 percent / I₂ / methanol / 0.5 h / Ambient temperature

With hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; iodine; triethylamine; dicyclohexyl-carbodiimide; In methanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.65.2227

Reference yield:

Boc-3-Me-D-Cys(Trt)-OSu (87242-69-1) → (5S,6S,10R,15aS)-5-tert-Butoxycarbonylamino-6-methyl-4,12,15-trioxo-dodecahydro-7,8-dithia-3a,11,14-triaza-cyclopentacyclotetradecene-10-carboxylic acid benzyl ester (141698-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / triethylamine (TEA) / dimethylformamide / 72 h / Ambient temperature

2: 1.) N-hydroxysuccinimide (HOSu), dicyclohexylcarbodiimide (DCC), 2.) triethylamine (TEA) / 1.) THF, RT, 2 h, 2.) DMF, RT, overnight

3: 90 percent / I₂ / methanol / 0.5 h / Ambient temperature

With 1-hydroxy-pyrrolidine-2,5-dione; iodine; triethylamine; dicyclohexyl-carbodiimide; In methanol; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.65.2227

upstream raw materials:

Boc-3-Me-Cys(Trt)-Pro-Gly-Cys(Acm)-OBzl

H-Cys(Acm)-OBzl hydrochloride

Boc-Gly-Cys(Acm)-OBzl

Boc-3-Me-Cys(Trt)-Pro-OH

Downstream raw materials:

(5S,6S,9R,14aS)-5-tert-Butoxycarbonylamino-6-methyl-4,11,14-trioxo-dodecahydro-7-thia-3a,10,13-triaza-cyclopentacyclotridecene-9-carboxylic acid benzyl ester

(S)-6-Benzyloxycarbonylamino-2-{[(5S,6S,9R,14aS)-6-methyl-4,11,14-trioxo-5-(2,2,2-trichloro-ethoxycarbonylamino)-dodecahydro-7-thia-3a,10,13-triaza-cyclopentacyclotridecene-9-carbonyl]-amino}-hexanoic acid tert-butyl ester

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