Trifluoro-methanesulfonic acid (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-yl ester

Base Information

Chemical Name:Trifluoro-methanesulfonic acid (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-yl ester
CAS No.:88670-01-3
Molecular Formula:C₁₈H₁₈F₃N₅O₆S
Molecular Weight:489.432
Hs Code.:

Synonyms:Trifluoro-methanesulfonic acid (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-yl ester

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Chemical Property of Trifluoro-methanesulfonic acid (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-yl ester

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Technology Process of Trifluoro-methanesulfonic acid (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-yl ester

There total 8 articles about Trifluoro-methanesulfonic acid (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-yl 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:

: 358-23-6
trifluoromethylsulfonic anhydride

: 88669-89-0
(2S,5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-3,7-dione

: 88670-01-3
Trifluoro-methanesulfonic acid (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-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at -78 ℃;
DOI:10.1021/ja00318a042

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 88670-01-3
Trifluoro-methanesulfonic acid (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-yl ester

Guidance literature:: Multi-step reaction with 7 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

: 88670-01-3
Trifluoro-methanesulfonic acid (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-yl ester

Guidance literature:: Multi-step reaction with 5 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