(3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

Base Information

Chemical Name:(3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate
CAS No.:1075206-57-3
Molecular Formula:C₄₃H₆₀N₂O₆SSi
Molecular Weight:761.111
Hs Code.:

Synonyms:(3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

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Chemical Property of (3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

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Technology Process of (3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

There total 9 articles about (3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate 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%

: 1075206-56-2
(3S,4R)-allyl 4-amino-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

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

: 1075206-57-3
(3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

Guidance literature:: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.3987/COM-07-S(N)5

Reference yield:

: 106391-88-2
(2R)-2-[(tert-butoxycarbonyl)amino]-3-methylbutylaldehyde

: 1075206-57-3
(3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 0.67 h / -78 °C

2.1: sulfuric acid; chromium(VI) oxide / water; acetone / 1 h / 20 °C

3.1: potassium borohydride / methanol / 5 h / -40 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

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

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

7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C

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

With 1H-imidazole; 2,6-dimethylpyridine; potassium borohydride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; chromium(VI) oxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1.2: Aldol coupling / 2.1: Jones oxidation;
DOI:10.3987/COM-07-S(N)5

Reference yield:

: 1075206-54-0
(3S,4R)-ethyl 4-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

: 1075206-57-3
(3S,4R)-allyl 4-[(S)-2-(tert-butoxycarbonylamino)-3-(tritylthio)propanamido]-3-(tert-butyldimethylsiloxy)-5-methylhexanoate

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C

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

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.3987/COM-07-S(N)5