(3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one

Base Information

• Chemical Name: (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one
• CAS No.: 132127-30-1
• Molecular Formula: C₁₅H₂₃NO₂Si
• Molecular Weight: 277.439
• Mol file: 132127-30-1.mol

Synonyms:(3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one

Chemical Property of (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one

There total 9 articles about (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-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: 90.0%

(3R,4S)-3-tert-butyldimethylsiloxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one (880781-88-4) → (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one (132127-30-1)

Guidance literature:

With ammonium cerium(IV) nitrate; water; In acetonitrile; at 0 ℃;

DOI:10.1016/j.tet.2007.05.031

Reference yield:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate (950586-04-6) → (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one (132127-30-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: 99 percent / MeMgBr / tetrahydrofuran / -78 - -10 °C

3: 90 percent / CAN; H₂O / acetonitrile / 0 °C

With 1H-imidazole; ammonium cerium(IV) nitrate; methylmagnesium bromide; water; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2007.05.031

Reference yield:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-tert-butyldimethylsiloxy-3-(4-methoxyphenylamino)-3-phenylpropanoate (950586-06-8) → (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one (132127-30-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / MeMgBr / tetrahydrofuran / -78 - -10 °C

2: 90 percent / CAN; H₂O / acetonitrile / 0 °C

With ammonium cerium(IV) nitrate; methylmagnesium bromide; water; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tet.2007.05.031

upstream raw materials:

N-benzylidene-1,1,1-trimethylsilanamine

(1R,2S)-2-Phenyl-1-cyclohexyl t-butyldimethylsilyloxyacetate

(E)-N-benzylidene-1,1,1-trimethylsilanamine

(tert-Butyl-dimethyl-silanyloxy)-acetic acid 2-phenyl-cyclohexyl ester

Downstream raw materials:

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

7-(triethylsilyl)baccatin III 13--(2'R,3'S)-3'-phenylisoserinate>

7-(triethylsilyl)baccatin III 13-

N-(4-azidobenzoyl)-N-debenzoyltaxol