(3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate

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Chemical Name:(3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate
CAS No.:1426828-65-0
Molecular Formula:C₃₉H₅₄N₂O₄SSi
Molecular Weight:675.02
Hs Code.:

Synonyms:(3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate

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Chemical Property of (3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate

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Technology Process of (3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate

There total 10 articles about (3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate 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: 88.0%

: 1426828-69-4
(3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate

: 1426828-65-0
(3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate

Guidance literature:: (3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate; With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h;

With methanol; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1016/j.ejmech.2012.12.023

Reference yield:

: 116662-96-5
(2R)-2-(1,1-dimethylethoxycarbonylamino)-4-methylpentanal

: 1426828-65-0
(3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.67 h / -78 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

3.1: sodium hydroxide / ethanol / 6 h / 20 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C

5.1: trimethylsilyl trifluoromethanesulfonate; 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

5.2: 1 h / 0 - 20 °C

6.1: trimethylsilyl trifluoromethanesulfonate; 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

6.2: 1 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.ejmech.2012.12.023

Reference yield:

: N-(tert-butoxycarbonyl)-S-trityl-D-cysteine

: 1426828-65-0
(3S,4R)-allyl 4-[(S)-2-amino-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-6-methylheptanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 3 h / 20 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate; 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

2.2: 1 h / 0 - 20 °C

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;
DOI:10.1016/j.ejmech.2012.12.023