(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

Base Information

Chemical Name:(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone
CAS No.:128971-90-4
Molecular Formula:C₂₄H₃₁NO₂SSi
Molecular Weight:425.667
Hs Code.:

Synonyms:(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

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Chemical Property of (3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

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Technology Process of (3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

There total 6 articles about (3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone 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:

: 128971-87-9
(3R,4S)-Benzyl 3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylate

: 128971-90-4
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / Ambient temperature

2: 72 percent / dimethylformamide; acetic acid / 40 - 50 °C

3: 1) NaOMe / 1) MeOH, -30 deg C, 15 min, 2) MeOH, a) -30 deg C, 30 min, b) 10 deg C, 10 min

With hydrogen; sodium methylate; palladium on activated charcoal; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo00304a024

Reference yield:

: 128971-84-6
(2S,3R)-Dibenzyl 2-Azido-3-<(tert-butyldiphenylsilyl)oxy>succinate

: 128971-90-4
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / PPh₃ / tetrahydrofuran; H₂O / 18 h / 60 °C

2: 1) Me₃SiCl, Et₃N, 2) t-BuMgCl / 1) Et₂O, 0 deg C, 1 h, 2) Et₂O, room temp., 18 h

3: 99 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / Ambient temperature

4: 72 percent / dimethylformamide; acetic acid / 40 - 50 °C

5: 1) NaOMe / 1) MeOH, -30 deg C, 15 min, 2) MeOH, a) -30 deg C, 30 min, b) 10 deg C, 10 min

With chloro-trimethyl-silane; tert-butylmagnesium chloride; hydrogen; sodium methylate; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo00304a024

Reference yield:

: 128971-86-8
(2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate

: 128971-90-4
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 1) Me₃SiCl, Et₃N, 2) t-BuMgCl / 1) Et₂O, 0 deg C, 1 h, 2) Et₂O, room temp., 18 h

2: 99 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / Ambient temperature

3: 72 percent / dimethylformamide; acetic acid / 40 - 50 °C

4: 1) NaOMe / 1) MeOH, -30 deg C, 15 min, 2) MeOH, a) -30 deg C, 30 min, b) 10 deg C, 10 min

With chloro-trimethyl-silane; tert-butylmagnesium chloride; hydrogen; sodium methylate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo00304a024