{2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester

Base Information

Chemical Name:{2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester
CAS No.:88670-00-2
Molecular Formula:C₂₇H₂₉N₇O₇S
Molecular Weight:595.636
Hs Code.:

{2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester

Synonyms:{2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester

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Chemical Property of {2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester

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Technology Process of {2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester

There total 9 articles about {2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic 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:

: 3587-60-8
Benzyloxymethyl chloride

: 88670-00-2
{2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

2: saponification

3: 1.) dibutylmagnesium; 2.) carbonyl diimidazole / 1.) THF, heptane, 0 deg C; 2.) THF

4: HF / H₂O; acetonitrile

5: Et₃N, p-(C₁₂H₂₅)C₆H₄SO₂N₃ / CH₂Cl₂

6: rhodium (II) acetate dimer / CH₂Cl₂ / Heating

7: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / -78 °C

With dirhodium tetraacetate; p-(C₁₂H₂₅)C₆H₄SO₂N₃; hydrogen fluoride; dibutylmagnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00318a042

Reference yield:

: 88669-70-9
(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one

: 88670-00-2
{2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) dibutylmagnesium; 2.) carbonyl diimidazole / 1.) THF, heptane, 0 deg C; 2.) THF

2: HF / H₂O; acetonitrile

3: Et₃N, p-(C₁₂H₂₅)C₆H₄SO₂N₃ / CH₂Cl₂

4: rhodium (II) acetate dimer / CH₂Cl₂ / Heating

5: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / -78 °C

With dirhodium tetraacetate; p-(C₁₂H₂₅)C₆H₄SO₂N₃; hydrogen fluoride; dibutylmagnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00318a042

Reference yield:

: 88669-73-2
(1-Benzyloxymethyl-1H-tetrazol-5-yl)-acetic acid ethyl ester

: 88670-00-2
{2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: saponification

2: 1.) dibutylmagnesium; 2.) carbonyl diimidazole / 1.) THF, heptane, 0 deg C; 2.) THF

3: HF / H₂O; acetonitrile

4: Et₃N, p-(C₁₂H₂₅)C₆H₄SO₂N₃ / CH₂Cl₂

5: rhodium (II) acetate dimer / CH₂Cl₂ / Heating

6: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / -78 °C

With dirhodium tetraacetate; p-(C₁₂H₂₅)C₆H₄SO₂N₃; hydrogen fluoride; dibutylmagnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00318a042