[(5S,11S,12R)-2-(4-Chloro-benzyloxy)-12-methyl-5-methylcarbamoyl-2,7,10-trioxo-1,3-dioxa-6,9-diaza-2λ⁵-phospha-cyclododec-11-yl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(5S,11S,12R)-2-(4-Chloro-benzyloxy)-12-methyl-5-methylcarbamoyl-2,7,10-trioxo-1,3-dioxa-6,9-diaza-2λ⁵-phospha-cyclododec-11-yl]-carbamic acid tert-butyl ester
• CAS No.: 123621-78-3
• Molecular Formula: C₂₂H₃₂ClN₄O₉P
• Molecular Weight: 562.944

Synonyms:

Chemical Property of [(5S,11S,12R)-2-(4-Chloro-benzyloxy)-12-methyl-5-methylcarbamoyl-2,7,10-trioxo-1,3-dioxa-6,9-diaza-2λ⁵-phospha-cyclododec-11-yl]-carbamic acid tert-butyl ester

Chemical Property:

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Useful:

Technology Process of [(5S,11S,12R)-2-(4-Chloro-benzyloxy)-12-methyl-5-methylcarbamoyl-2,7,10-trioxo-1,3-dioxa-6,9-diaza-2λ⁵-phospha-cyclododec-11-yl]-carbamic acid tert-butyl ester

There total 7 articles about [(5S,11S,12R)-2-(4-Chloro-benzyloxy)-12-methyl-5-methylcarbamoyl-2,7,10-trioxo-1,3-dioxa-6,9-diaza-2λ⁵-phospha-cyclododec-11-yl]-carbamic acid tert-butyl 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:

Boc-Gly-Ser(OBn)-NHCH3 (123621-80-7) → [(5S,11S,12R)-2-(4-Chloro-benzyloxy)-12-methyl-5-methylcarbamoyl-2,7,10-trioxo-1,3-dioxa-6,9-diaza-2λ5-phospha-cyclododec-11-yl]-carbamic acid tert-butyl ester (123621-78-3,123673-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) TFA, 2) N,N-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole, methylmorpholine / 1) CH₂Cl₂, 0 deg C, 1 h, 2) THF, room temperature, 3 h

2: 98 percent / H₂ / 10percent Pd/C / methanol

3: 1) diisopropylethylamine, 2) 3-chloroperbenzoic acid / 1) CH₂Cl₂, CH₃CN, room temperature, 3 h, 2a) 0 deg C to room temperature, b) room temperature, 20 min

With 2-methylmorpholine; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00066a026

Reference yield:

Boc-Thr(OBn)-Gly-Ser(OBn)-NHCH3 (123621-81-8) → [(5S,11S,12R)-2-(4-Chloro-benzyloxy)-12-methyl-5-methylcarbamoyl-2,7,10-trioxo-1,3-dioxa-6,9-diaza-2λ5-phospha-cyclododec-11-yl]-carbamic acid tert-butyl ester (123621-78-3,123673-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂ / 10percent Pd/C / methanol

2: 1) diisopropylethylamine, 2) 3-chloroperbenzoic acid / 1) CH₂Cl₂, CH₃CN, room temperature, 3 h, 2a) 0 deg C to room temperature, b) room temperature, 20 min

With hydrogen; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00066a026

Reference yield:

(S)-2-(2-Amino-acetylamino)-3-benzyloxy-N-methyl-propionamide → [(5S,11S,12R)-2-(4-Chloro-benzyloxy)-12-methyl-5-methylcarbamoyl-2,7,10-trioxo-1,3-dioxa-6,9-diaza-2λ5-phospha-cyclododec-11-yl]-carbamic acid tert-butyl ester (123621-78-3,123673-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1: DCC, 4-ethylmorpholine / various solvent(s)

2: 90 percent / H₂ / Pd/C / methanol

3: 1.) 1H-tetrazole, 2.) t-BuOOH / 1.) MeCN

With N-ethylmorpholine;; 1H-tetrazole; tert.-butylhydroperoxide; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol;

DOI:10.1021/ja00207a019

upstream raw materials:

4-chlorobenzyl phosphorodichloridite

Boc-Thr(OH)-Gly-Ser(OH)-NHCH₃

4-chlorobenzyl bis(N,N-diisopropyl)phosphorodiamidite

N-Boc-O-benzyl-L-threonine

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