(2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol

Base Information

Chemical Name:(2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol
CAS No.:173105-96-9
Molecular Formula:C₂₀H₃₃NO₃Si
Molecular Weight:363.572
Hs Code.:

Synonyms:(2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol

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Chemical Property of (2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol

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Technology Process of (2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol

There total 9 articles about (2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol 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: 52.0%

: 173105-95-8
(2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinecarboxaldehyde

: 173105-96-9
(2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 40 ℃; for 1.5h;
DOI:10.1016/0040-4020(95)00902-7

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 173105-96-9
(2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / Et₃N / dimethylformamide / 6 h / Ambient temperature

2: 100 percent / 80percent m-CPBA / CH₂Cl₂

3: 100 percent / 2,6-lutidine, trifluoroacetic anhydride / 0 °C

4: 52 percent / NaBH₄ / ethanol / 1.5 h / 40 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(95)00902-7

Reference yield:

: (3S,4S)-3-<(S)-1-(formyloxy)ethyl>-1-<(S)-1-phenylethyl>-4-<(phenylthio)methyl>-2-azetidinone

: 173105-96-9
(2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(S)-1-phenylethyl>-4-oxo-2-azetidinemethanol

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / 10percent aq. HCl / methanol / 5 h / Ambient temperature

2: 99 percent / Et₃N / dimethylformamide / 6 h / Ambient temperature

3: 100 percent / 80percent m-CPBA / CH₂Cl₂

4: 100 percent / 2,6-lutidine, trifluoroacetic anhydride / 0 °C

5: 52 percent / NaBH₄ / ethanol / 1.5 h / 40 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(95)00902-7