(3S,4S)-N-(tert-butyldimethylsilyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one

Base Information

• Chemical Name: (3S,4S)-N-(tert-butyldimethylsilyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one
• CAS No.: 211816-27-2
• Molecular Formula: C₂₆H₄₁NO₂Si
• Molecular Weight: 427.703
• Mol file: 211816-27-2.mol

Synonyms:

Chemical Property of (3S,4S)-N-(tert-butyldimethylsilyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-N-(tert-butyldimethylsilyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one

There total 16 articles about (3S,4S)-N-(tert-butyldimethylsilyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-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: 15.0%

(2R,3S)-N-(tert-butyldimethylsilyl)-3-methyl-4-oxoazetidine-2-carbaldehyde (211816-31-8) + (2E,4S,5S)-1-diphenylphosphinoyl-5-methoxy-2,4-dimethyl-6-phenylhex-2-ene (211816-18-1) → (3S,4S)-N-(tert-butyldimethylsilyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one (211816-27-2)

Guidance literature:

With base;

DOI:10.1016/S0040-4039(98)00946-0

Reference yield:

(2R)-benzyl N-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate (185387-26-2) → (3S,4S)-N-(tert-butyldimethylsilyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one (211816-27-2)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄, LiBr, H₂O / tetrahydrofuran / 0.67 h / Ambient temperature

2: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h

3: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, -78 deg C, 15 min; -78 deg C to r.t., 1 h

4: 1.) NaHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to r.t.; r.t., 2 h

With sodium tetrahydroborate; oxalyl dichloride; water; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran;

Reference yield:

(3S,4R)-N-(tert-butyldimethylsilyl)-4-hydroxymethyl-3-methylazetidin-2-one (211816-39-6) → (3S,4S)-N-(tert-butyldimethylsilyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one (211816-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, -78 deg C, 15 min; -78 deg C to r.t., 1 h

2: 1.) NaHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to r.t.; r.t., 2 h

With oxalyl dichloride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine;

upstream raw materials:

(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-enyl(triphenyl)phosphonium bromide

(2R,3S)-N-(tert-butyldimethylsilyl)-3-methyl-4-oxoazetidine-2-carbaldehyde

(2E,4S,5S)-1-diphenylphosphinoyl-5-methoxy-2,4-dimethyl-6-phenylhex-2-ene

2-<<(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-enyl>sulfonyl>benzothiazole

Downstream raw materials:

(3S,4S)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one

(3S,4S)-N-(tert-butoxycarbonyl)-4-<(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl>-3-methylazetidin-2-one