(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

Chemical Name:(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
CAS No.:124831-33-0
Molecular Formula:C₁₅H₁₇NO₃S
Molecular Weight:291.371
Hs Code.:

Synonyms:(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

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Chemical Property of (2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

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Technology Process of (2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 6 articles about (2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 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:

: 128971-79-9
(3S,4R)-4-<(2-Methyl-3-buten-2-yl)thio>-3-(trimethylsilyl)-2-azetidinone

: 124831-33-0
(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / i-Pr₂NEt, N,N-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / Ambient temperature

2: 1) O₃, 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 2) 0 deg C, 15 min

3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h

4: 72 percent / Et₃N, acetyl chloride / 20 h / 0 °C

5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C, 2 min

With dmap; dimethylsulfide; potassium tert-butylate; tetrabutyl ammonium fluoride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; In dichloromethane;
DOI:10.1021/jo00304a024

Reference yield:

: 124831-31-8
(3S,4R)-1-(tert-Butyldimethylsilyl)-4-<(2-methyl-3-oxo-2-propyl)thio>-3-(trimethylsilyl)-2-azetidinone

: 124831-33-0
(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) KOt-Bu 2.) acetyl chloride, Et₃N / 1.) t-BuOH, THF 2.) 10 gradC

2: 1.) tetrabutylammonium fluoride 2.) ozone / 1.) THF, -78 gradC 2.) CH₂Cl₂

With potassium tert-butylate; tetrabutyl ammonium fluoride; ozone; triethylamine; acetyl chloride;
DOI:10.1016/S0040-4039(01)80395-6

Reference yield:

: 124831-32-9
(3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

: 124831-33-0
(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; ozone; Yield given. Multistep reaction; 1) THF, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C, 2 min;
DOI:10.1021/jo00304a024