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

Base Information

• Chemical Name: 7-O-(triethylsilyl)baccatrin III 13-O-<(2R,3S)-N-benzoyl-2-O-(tert-butyldimethylsilyl)-3-cyclohexylisoserinate>
• CAS No.: 160239-19-0
• Molecular Formula: C₅₉H₈₅NO₁₄Si₂
• Molecular Weight: 1088.49
• Mol file: 160239-19-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 7-O-(triethylsilyl)baccatrin III 13-O-<(2R,3S)-N-benzoyl-2-O-(tert-butyldimethylsilyl)-3-cyclohexylisoserinate> 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: 71.0%

7-(triethylsilyl)baccatin III (115437-21-3) + (3R,4S)-1-benzoyl-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone (160239-18-9) → 7-O-(triethylsilyl)baccatrin III 13-O-<(2R,3S)-N-benzoyl-2-O-(tert-butyldimethylsilyl)-3-cyclohexylisoserinate> (160239-19-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 25 - 35 ℃; for 1.5h;

DOI:10.1021/jm00046a018

Reference yield:

(3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one (132127-30-1) → 7-O-(triethylsilyl)baccatrin III 13-O-<(2R,3S)-N-benzoyl-2-O-(tert-butyldimethylsilyl)-3-cyclohexylisoserinate> (160239-19-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 31 mg / H₂ / 3percent Pt/C / ethyl acetate / 12 h / 2844.3 Torr

2: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

3: 71 percent / NaH / tetrahydrofuran / 1.5 h / 25 - 35 °C

With dmap; hydrogen; sodium hydride; triethylamine; platinum on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jm00046a018

Reference yield:

benzoyl chloride (98-88-4) → 7-O-(triethylsilyl)baccatrin III 13-O-<(2R,3S)-N-benzoyl-2-O-(tert-butyldimethylsilyl)-3-cyclohexylisoserinate> (160239-19-0)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/jm00046a018

upstream raw materials:

7-(triethylsilyl)baccatin III

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

benzoyl chloride

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

Refernces