(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one

Base Information

Chemical Name:(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one
CAS No.:88669-93-6
Molecular Formula:C₂₃H₂₃N₅O₃S
Molecular Weight:449.533
Hs Code.:

Synonyms:(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one

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Chemical Property of (5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one

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Technology Process of (5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one

There total 9 articles about (5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one 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

: 88669-93-6
(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one

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

: 88669-93-6
(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one

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:

: 102985-97-7
(1-Benzyloxymethyl-1H-tetrazol-5-yl)-acetic acid

: 88669-93-6
(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one

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