[(1R,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

Base Information

• Chemical Name: [(1R,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS No.: 71610-00-9
• Molecular Formula: C45H53NO14
• Molecular Weight: 831.914
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID301317229
• Nikkaji Number: J55.709I
• Mol file: 71610-00-9.mol

Synonyms:DTXSID301317229

Chemical Property of [(1R,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 139-141oC
• Refractive Index: 1.614
• Boiling Point: 929.5 °C at 760 mmHg
• PKA: 11.95±0.20(Predicted)
• Flash Point: 516 °C
• PSA: 221.29000
• Density: 1.36 g/cm³
• LogP: 3.77900
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: 14?mg/mL, soluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 14
• Exact Mass: 831.34660536
• Heavy Atom Count: 60
• Complexity: 1790

Purity/Quality:

99% ^*data from raw suppliers

Cephalomannine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• Isomeric SMILES: C/C=C(\C)/C(=O)N[C@@H](C1=CC=CC=C1)[C@H](C(=O)O[C@H]2C[C@@]3([C@H]([C@H]4[C@@]([C@H](C[C@@H]5[C@]4(CO5)OC(=O)C)O)(C(=O)[C@@H](C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• Uses: Cephalomannine is an active anti-cancer agent obtained from Taxus yunnanensis and has an antineoplastic effect on tumors found in mice. Cephalomannine is a chemotherapy drug that is given as a treatment for some types of cancer. Cephalomannine is most com Antitumor, antiproliferative. similar anti-cancer function as Taxol

Technology Process of [(1R,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

There total 9 articles about [(1R,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 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%

→ cephalomannine (71610-00-9)

Guidance literature:

Reference yield: 81.0%

C2HF3O2*C40H47NO13 + (E)-2-methylbut-2-enoyl chloride (35660-94-7) → cephalomannine (71610-00-9)

Guidance literature:

Reference yield:

2'-acetylcephalomannine (861856-91-9) → cephalomannine (71610-00-9)

Guidance literature:

With methanol; dimethyl amine; at 3 ℃; for 1.5h;

upstream raw materials:

C₄₇H₅₂Cl₃NO₁₅

7-trichloroacetyl-3'-debenzoylpaclitaxel

C₄₅H₄₈Cl₅NO₁₄

7-trichloroacetylbaccatin III

Downstream raw materials:

7-epi-baccatin III

10-deacetylbaccatin III

(2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester

baccatin III

Refernces

• 1、 -. "Process for the Preparation of Synthetic Taxanes". Page/Page column 6. . Retrieved 2008/12/09.
• 2、 -. "Synthesis of taxol, analogs and intermediates with variable A-nng side chains". Page 8-9. . Retrieved 2010/01/31.