(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone

Base Information

Chemical Name:(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone
CAS No.:220430-36-4
Molecular Formula:C₃₈H₅₇NO₇Si₂
Molecular Weight:696.044
Hs Code.:

(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone

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Chemical Property of (3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone

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Technology Process of (3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone

There total 8 articles about (3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone 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: 88.0%

: 20578-60-3
glyoxylic acid benzhydryl ester

: 220430-35-3
(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-2-azetidinone

: 220430-36-4
(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone

Guidance literature:: In toluene; for 3h; Heating;
DOI:10.3987/COM-98-8302

Reference yield:

: 119105-31-6
6-bromocyclohex-1-enecarboxylic acid ethyl ester

: 220430-36-4
(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 7 steps

1: 30 percent / zinc dust / tetrahydrofuran / 1 h / 40 °C

2: 60 percent / DIBAL-H / toluene; methanol / -78 - 0 °C

3: 85 percent / tri-n-butylphosphine / CH₂Cl₂ / 1 h / -78 °C

4: 50 percent / 30 percent H₂O₂ / pyridine; H₂O / 0.5 h / Ambient temperature

5: 83 percent / O₃; dimethyl sulfide / CH₂Cl₂; methanol / 0.17 h / -78 °C

6: imidazole / dimethylformamide / 1 h / 0 °C

7: 88 percent / toluene / 3 h / Heating

With 1H-imidazole; dimethylsulfide; tributylphosphine; dihydrogen peroxide; diisobutylaluminium hydride; ozone; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.3987/COM-98-8302

Reference yield:

: 28469-52-5
6-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

: 220430-36-4
(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(2-diphenylmethoxycarbonyl-1-hydroxyethyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 8 steps

1: 82 percent / NBS, dimethyl sulfide / CH₂Cl₂ / 2.5 h / Ambient temperature

2: 30 percent / zinc dust / tetrahydrofuran / 1 h / 40 °C

3: 60 percent / DIBAL-H / toluene; methanol / -78 - 0 °C

4: 85 percent / tri-n-butylphosphine / CH₂Cl₂ / 1 h / -78 °C

5: 50 percent / 30 percent H₂O₂ / pyridine; H₂O / 0.5 h / Ambient temperature

6: 83 percent / O₃; dimethyl sulfide / CH₂Cl₂; methanol / 0.17 h / -78 °C

7: imidazole / dimethylformamide / 1 h / 0 °C

8: 88 percent / toluene / 3 h / Heating

With 1H-imidazole; N-Bromosuccinimide; dimethylsulfide; tributylphosphine; dihydrogen peroxide; diisobutylaluminium hydride; ozone; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.3987/COM-98-8302