(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Base Information

Chemical Name:(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
CAS No.:127941-60-0
Molecular Formula:C₂₇H₃₇N₃O₈S₂Si
Molecular Weight:623.824
Hs Code.:

(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Synonyms:(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

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Chemical Property of (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

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Technology Process of (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

There total 1 articles about (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 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: 70.0%

: 65750-59-6
2-(4-nitrobenzyloxycarbonylamino)ethanethiol

: 127941-60-0
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -40 - -20 ℃;
DOI:10.1016/S0040-4039(00)87662-5

Reference yield: 56.0%

: 127941-60-0
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

: (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(00)87662-5

Reference yield:

: 127941-60-0
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

: Potassium; (5R,6S)-6-((R)-1-hydroxy-ethyl)-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 56 percent / Bu₄NF, HOAc / tetrahydrofuran / Ambient temperature

2: 72 percent / <Φ3P>4Pd, Φ3P, Me(CH2)3CH(Et)CO2K / ethyl acetate

With <Φ3P>4Pd; Φ3P; tetrabutyl ammonium fluoride; potassium 2-ethylhexanoate; acetic acid; In tetrahydrofuran; ethyl acetate;
DOI:10.1016/S0040-4039(00)87662-5