(3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-2-one
• CAS No.: 146861-05-4
• Molecular Formula: C₄₄H₄₉NO₅Si
• Molecular Weight: 699.962
• Mol file: 146861-05-4.mol

Synonyms:(3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-2-one

Chemical Property of (3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-2-one

There total 1 articles about (3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-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: 75.0%

Benzyloxyacetyl chloride (19810-31-2) + [(2S,4S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-pent-(E)-ylidene]-(4-methoxy-phenyl)-amine → (3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-2-one (146861-05-4)

Guidance literature:

With triethylamine; In dichloromethane; at -78 - 20 ℃; for 24h; other imines, other alkoxyacetyl chlorides, stereoselectivity;

DOI:10.1021/jo00059a003

Reference yield: 50.0%

(3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-2-one (146861-05-4) → (3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-azetidin-2-one (146861-06-5)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at -5 ℃; for 0.25h;

DOI:10.1021/jo00059a003

Reference yield:

(3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-1-(4-methoxy-phenyl)-azetidin-2-one (146861-05-4) → (2S,3R,4S,6S)-2,4-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-heptanoic acid methyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 0.25 h / -5 °C

2: ClSiMe₃ / 0 deg C to RT, 2 h

3: NEt₃ / CH₂Cl₂

With chloro-trimethyl-silane; ammonium cerium(IV) nitrate; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1021/jo00059a003

upstream raw materials:

Benzyloxyacetyl chloride

Downstream raw materials:

(3S,4R)-3-Benzyloxy-4-[(1S,3S)-1-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butyl]-azetidin-2-one

(2S,3R,4S,6S)-3-Amino-2,4-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-heptanoic acid methyl ester