13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III

Base Information

• Chemical Name: 13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III
• CAS No.: 850933-54-9
• Molecular Formula: C₆₂H₆₃NO₁₈
• Molecular Weight: 1110.18
• Mol file: 850933-54-9.mol

Synonyms:13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III

Chemical Property of 13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III

There total 5 articles about 13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin 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: 80.0%

(4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-benzyl ester + C-7,C-10-dibenzyloxycarbonyl-10-deacetyl baccatin III (194864-02-3) → 13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III (850933-54-9) + C70H69NO19

Guidance literature:

(4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-benzyl ester; C-7,C-10-dibenzyloxycarbonyl-10-deacetyl baccatin III; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 5h;

DOI:10.1021/jm049344g

Reference yield:

(4S,5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-benzyloxycarbonyl-1,3-oxazolidine → 13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III (850933-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. KOH / methanol / 2 h / 20 °C

2.1: DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

2.2: 80 percent / p-toluenesulfonic acid / methanol / 5 h / 20 °C

With dmap; potassium hydroxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1021/jm049344g

Reference yield:

(2R,3S)-3-phenylisoserine hydrochloride (132201-32-2,161453-08-3,949459-75-0,521059-43-8) → 13-(3'-N-benzyloxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III (850933-54-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: SOCl₂ / 20 °C

2.1: aq. NaHCO₃ / CH₂Cl₂ / 3 h / 20 °C

3.1: 469 mg / pyridinium p-toluenesulfonate / toluene / Heating

4.1: aq. KOH / methanol / 2 h / 20 °C

5.1: DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

5.2: 80 percent / p-toluenesulfonic acid / methanol / 5 h / 20 °C

With dmap; potassium hydroxide; thionyl chloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; toluene;

DOI:10.1021/jm049344g

upstream raw materials:

C-7,C-10-dibenzyloxycarbonyl-10-deacetyl baccatin III

(2R,3S)-3-phenylisoserine hydrochloride

(2R,3S)-3-phenylisoserine methyl ester

(-)-(2R,3S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Downstream raw materials:

13-(3'-N-benzyloxycarbonyl-2'-tert-butoxycarbonylphenylisoserine)-10-deacetyl-7,10-dibenzyloxycarbonylbaccatin III

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Refernces