(3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone
• CAS No.: 160239-17-8
• Molecular Formula: C₁₅H₂₉NO₂Si
• Molecular Weight: 283.486
• Mol file: 160239-17-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-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:

(3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one (132127-30-1) → (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone (160239-17-8)

Guidance literature:

With hydrogen; platinum on activated charcoal; In ethyl acetate; for 12h; under 2844.3 Torr;

DOI:10.1021/jm00046a018

Reference yield: 96.0%

benzoyl chloride (98-88-4) + (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone (160239-17-8) → (3R,4S)-1-benzoyl-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone (160239-18-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jm00046a018

Reference yield:

(3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone (160239-17-8) → baccatrin III 13-O-<(2R,3S)-N-benzoyl-3-cyclohexylisoserinate>

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

2: 71 percent / NaH / tetrahydrofuran / 1.5 h / 25 - 35 °C

3: 84 percent / pyridinium hydrofluoride / pyridine / 3 h

With dmap; sodium hydride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jm00046a018

upstream raw materials:

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

Downstream raw materials:

(3R,4S)-1-benzoyl-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone

7-O-(triethylsilyl)baccatrin III 13-O-<(2R,3S)-N-benzoyl-2-O-(tert-butyldimethylsilyl)-3-cyclohexylisoserinate>