(2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol

Base Information

Chemical Name:(2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol
CAS No.:799559-97-0
Molecular Formula:C₂₃H₄₁NO₄SSi
Molecular Weight:455.734
Hs Code.:

Synonyms:(2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol

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Chemical Property of (2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol

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Technology Process of (2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol

There total 5 articles about (2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol 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: 89.0%

: 108-98-5
thiophenol

: 799559-79-8
(S)-[(S)-1-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsiloxy)butyl]oxirane

: 799559-97-0
(2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol

Guidance literature:: With triethylamine; In methanol; for 1.5h; Heating;
DOI:10.1021/jo0268456

Reference yield:

(E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol: 98897-64-4
(E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol

: 799559-97-0
(2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol

Guidance literature:: Multi-step reaction with 5 steps

1: Ti(O-i-Pr)4; D(-)-DIPT; t-BuOOH / CH₂Cl₂ / -20 °C

2: 55 percent / Ti(O-i-Pr)2(N₃)2 / benzene / Heating

3: 85 percent / H₂ / Pd/C / ethyl acetate / 20 °C

4: 81 percent / Ph₃P; diisopropyl azodicarboxylate / CHCl₃ / 7 h / Heating

5: 89 percent / Et₃N / methanol / 1.5 h / Heating

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diisopropoxytitanium diazide; di-isopropyl azodicarboxylate; hydrogen; D-(-)-diisopropyl tartrate; triethylamine; triphenylphosphine; palladium on activated charcoal; In methanol; dichloromethane; chloroform; ethyl acetate; benzene; 1: asymmetric Sharpless epoxidation / 4: Mitsunobu cyclization;
DOI:10.1021/jo0268456

Reference yield:

: 440083-43-2
(2S,3S)-6-(tert-butyldimethylsilyl)oxy-2,3-epoxyhexan-1-ol

: 799559-97-0
(2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol

Guidance literature:: Multi-step reaction with 4 steps

1: 55 percent / Ti(O-i-Pr)2(N₃)2 / benzene / Heating

2: 85 percent / H₂ / Pd/C / ethyl acetate / 20 °C

3: 81 percent / Ph₃P; diisopropyl azodicarboxylate / CHCl₃ / 7 h / Heating

4: 89 percent / Et₃N / methanol / 1.5 h / Heating

With diisopropoxytitanium diazide; di-isopropyl azodicarboxylate; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In methanol; chloroform; ethyl acetate; benzene; 3: Mitsunobu cyclization;
DOI:10.1021/jo0268456