(5R,6S)-3-(3-Azido-propylsulfanyl)-6-((R)-1-hydroxy-ethyl)-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)-3-(3-Azido-propylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:81036-50-2
Molecular Formula:C₁₈H₁₉N₅O₆S₂
Molecular Weight:465.511
Hs Code.:

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

There total 7 articles about (5R,6S)-3-(3-Azido-propylsulfanyl)-6-((R)-1-hydroxy-ethyl)-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: 94.0%

: 81036-42-2
(5R,6S)-3-(3-Azido-propylsulfanyl)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

: 81036-50-2
(5R,6S)-3-(3-Azido-propylsulfanyl)-6-((R)-1-hydroxy-ethyl)-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:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 81036-50-2
(5R,6S)-3-(3-Azido-propylsulfanyl)-6-((R)-1-hydroxy-ethyl)-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 7 steps

1: sodium methoxide / methanol / 0.33 h / 0 °C

2: 97 percent / benzene / 13 h / Heating

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

4: 66 percent / hydroquinone / xylene / 12 h / 125 - 130 °C

5: 43 percent / tetrabutylammonium fluoride / acetic acid / 3 h / Ambient temperature

6: 100 percent / triphenylphosphine, hydrogen azide (in benzene), diethyl azodicarboxylate / tetrahydrofuran / 0.17 h / 0 °C

7: 94 percent / tetrabutylammonium fluoride / acetic acid / 14 h

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

Reference yield:

: 81036-30-8
{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(tert-butyl-dimethyl-silanyloxy)-propylsulfanylthiocarbonylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester

: 81036-50-2
(5R,6S)-3-(3-Azido-propylsulfanyl)-6-((R)-1-hydroxy-ethyl)-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 5 steps

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

2: 66 percent / hydroquinone / xylene / 12 h / 125 - 130 °C

3: 43 percent / tetrabutylammonium fluoride / acetic acid / 3 h / Ambient temperature

4: 100 percent / triphenylphosphine, hydrogen azide (in benzene), diethyl azodicarboxylate / tetrahydrofuran / 0.17 h / 0 °C

5: 94 percent / tetrabutylammonium fluoride / acetic acid / 14 h

With 2,6-dimethylpyridine; hydrogen azide; thionyl chloride; tetrabutyl ammonium fluoride; hydroquinone; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; acetic acid; xylene;
DOI:10.1248/cpb.29.3158