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

Base Information

Chemical Name:(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-nitro-benzyloxycarbonylamino)-butylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:81036-46-6
Molecular Formula:C₂₇H₂₈N₄O₁₀S₂
Molecular Weight:632.672
Hs Code.:

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

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

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Chemical Property of (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-nitro-benzyloxycarbonylamino)-butylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-nitro-benzyloxycarbonylamino)-butylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 11 articles about (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-nitro-benzyloxycarbonylamino)-butylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl 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: 92.0%

: 81036-35-3
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(4-nitro-benzyloxycarbonylamino)-butylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

: 81036-46-6
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-nitro-benzyloxycarbonylamino)-butylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In acetic acid; for 14h;
DOI:10.1248/cpb.29.3158

Reference yield:

: 63216-42-2
γ-<<(p-nitrobenzyl)oxycarbonyl>amino>butyric acid

: 81036-46-6
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-nitro-benzyloxycarbonylamino)-butylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: triethylamine / tetrahydrofuran

2: NaBH₄

5: sodium methylate / methanol / 0.33 h / 0 °C

6: methanol / 0.33 h / 0 °C

7: 78 percent / benzene / 22 h / Heating

8: 1.)thionyl chloride, 2,6-lutidine 2.) 2,6-lutidine / 1.) THF, -15 deg C, 15 min, 2.) THF, 75 deg C, 42 h

9: 58 percent / hydroquinone / xylene / 16 h / 125 - 130 °C

10: 92 percent / tetrabutylammonium fluoride / acetic acid / 14 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; thionyl chloride; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; hydroquinone; In tetrahydrofuran; methanol; acetic acid; xylene; benzene;
DOI:10.1248/cpb.29.3158

Reference yield:

: 81036-23-9
(4-Hydroxy-butyl)-carbamic acid 4-nitro-benzyl ester

: 81036-46-6
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-nitro-benzyloxycarbonylamino)-butylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

3: sodium methylate / methanol / 0.33 h / 0 °C

4: methanol / 0.33 h / 0 °C

5: 78 percent / benzene / 22 h / Heating

6: 1.)thionyl chloride, 2,6-lutidine 2.) 2,6-lutidine / 1.) THF, -15 deg C, 15 min, 2.) THF, 75 deg C, 42 h

7: 58 percent / hydroquinone / xylene / 16 h / 125 - 130 °C

8: 92 percent / tetrabutylammonium fluoride / acetic acid / 14 h

With 2,6-dimethylpyridine; thionyl chloride; tetrabutyl ammonium fluoride; sodium methylate; hydroquinone; In methanol; acetic acid; xylene; benzene;
DOI:10.1248/cpb.29.3158