1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III

Base Information

• Chemical Name: 1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III
• CAS No.: 181419-96-5
• Molecular Formula: C₅₈H₈₅NO₁₄Si₂
• Molecular Weight: 1076.48
• Mol file: 181419-96-5.mol

Synonyms:1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III

Chemical Property of 1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III

There total 2 articles about 1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III 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: 82.0%

tert-butyl (3R,4S)-2-oxo-4-phenyl-3-(triethylsilyloxy)azetidine-1-carboxylate (149198-47-0) + 10-O-allyl-10-deacetyl-7-O-triethylsilylbaccatin III (181419-93-2) → 1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III (181419-96-5)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -45 ℃; for 0.25h;

DOI:10.1248/cpb.46.770

Reference yield:

7-triethylsilyl-10-deacetylbaccatin III (115437-18-8) → 1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III (181419-96-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, DMSO, 0 deg C, 3 h

2: 82 percent / LiHMDS / tetrahydrofuran / 0.25 h / -45 °C

With n-butyllithium; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1248/cpb.46.770

Reference yield:

1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III (181419-96-5) → C57H85NO15Si2

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; for 1h; Ambient temperature;

DOI:10.1248/cpb.46.770

upstream raw materials:

tert-butyl (3R,4S)-2-oxo-4-phenyl-3-(triethylsilyloxy)azetidine-1-carboxylate

10-O-allyl-10-deacetyl-7-O-triethylsilylbaccatin III

7-triethylsilyl-10-deacetylbaccatin III

Downstream raw materials:

13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-10-O-formylmethyl-7-O-triethylsilylbaccatin

C₆₁H₉₂N₂O₁₅Si₂

C₆₁H₉₂N₂O₁₄SSi₂