(alphaR,betaS)-alpha-(Chloroacetoxy)-beta-(benzoylamino)benzenepropionic acid 1,7beta-dihydroxy-2alpha-(benzoyloxy)-4,10beta-diacetoxy-9-oxo-5beta,20-epoxytaxa-11-ene-13alpha-yl ester

Base Information

• Chemical Name: (alphaR,betaS)-alpha-(Chloroacetoxy)-beta-(benzoylamino)benzenepropionic acid 1,7beta-dihydroxy-2alpha-(benzoyloxy)-4,10beta-diacetoxy-9-oxo-5beta,20-epoxytaxa-11-ene-13alpha-yl ester
• CAS No.: 152565-19-0
• Molecular Formula: C₄₉H₅₂ClNO₁₅
• Molecular Weight: 930.403
• Nikkaji Number: J1.607.633C
• Mol file: 152565-19-0.mol

Synonyms:SCHEMBL12854925;(alphaR,betaS)-alpha-(Chloroacetoxy)-beta-(benzoylamino)benzenepropionic acid 1,7beta-dihydroxy-2alpha-(benzoyloxy)-4,10beta-diacetoxy-9-oxo-5beta,20-epoxytaxa-11-ene-13alpha-yl ester

Chemical Property of (alphaR,betaS)-alpha-(Chloroacetoxy)-beta-(benzoylamino)benzenepropionic acid 1,7beta-dihydroxy-2alpha-(benzoyloxy)-4,10beta-diacetoxy-9-oxo-5beta,20-epoxytaxa-11-ene-13alpha-yl ester

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 17
• Exact Mass: 929.3025476
• Heavy Atom Count: 66
• Complexity: 1940

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)OC(=O)CCl)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)OC(=O)CCl)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C

Technology Process of (alphaR,betaS)-alpha-(Chloroacetoxy)-beta-(benzoylamino)benzenepropionic acid 1,7beta-dihydroxy-2alpha-(benzoyloxy)-4,10beta-diacetoxy-9-oxo-5beta,20-epoxytaxa-11-ene-13alpha-yl ester

There total 2 articles about (alphaR,betaS)-alpha-(Chloroacetoxy)-beta-(benzoylamino)benzenepropionic acid 1,7beta-dihydroxy-2alpha-(benzoyloxy)-4,10beta-diacetoxy-9-oxo-5beta,20-epoxytaxa-11-ene-13alpha-yl ester 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: 100.0%

taxol (33069-62-4) + Chloroacetic anhydride (541-88-8) → taxol-2'-chloroacetyl (152565-19-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/ol035234c

Reference yield:

vinyl chloroacetate (2549-51-1) + taxol (33069-62-4) → C49H52ClNO15 + taxol-2'-chloroacetyl (152565-19-0)

Guidance literature:

With thermolysin from Bacillus thermoproteolyticus Rokko; In tert-Amyl alcohol; at 35 ℃; for 96h;

DOI:10.1021/ja973103z

Reference yield: 75.0%

taxol-2'-chloroacetyl (152565-19-0) + NH2-L-Cys-(D-Arg)8-NH2 → C100H155N35O24S*9C2HF3O2

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/ol035234c

upstream raw materials:

vinyl chloroacetate

taxol

Chloroacetic anhydride

Downstream raw materials:

taxol

CG 1040

Refernces

• 1、 Kirschberg, Thorsten A.,VanDeusen, Chris L.,Rothbard, Jonathan B.,Yang, Michael,Wender, Paul A.. "Arginine-Based Molecular Transporters: The Synthesis and Chemical Evaluation of Releasable Taxol-Transporter Conjugates". . p. 3459 - 3462. Retrieved 2007/10/03.
• 2、 Khmelnitsky,Budde,Arnold,Usyatinsky,Clark,Dordick. "Synthesis of water-soluble paclitaxel derivatives by enzymatic acylation [10]". . p. 11554 - 11555. Retrieved 2007/10/03.