Isocephalomannine

Base Information

• Chemical Name: Isocephalomannine
• CAS No.: 173101-54-7
• Molecular Formula: C45H53NO14
• Molecular Weight: 831.90100
• European Community (EC) Number: 692-826-9
• UNII: S8ZT32GU6D
• DSSTox Substance ID: DTXSID10472971
• Wikidata: Q72535035
• Mol file: 173101-54-7.mol

Synonyms:Isocephalomannine;Iso Cephalomannine;173101-54-7;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] (E)-2-methylbut-2-enoate;2-Debenzoyl-2-tigloylpaclitaxel;S8ZT32GU6D;YJXDCLDHHJRTGV-WBYYIXQISA-;DTXSID10472971;2-O-debenzoyl-2-O-tigloylpaclitaxel;PACLITAXEL IMPURITY A [EP IMPURITY];2-Debenzoyl Paclitaxel-2-(2-Methyl-2-Butenoate);(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(acetyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-12-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (alphaR,betaS)-beta-(benzoylamino)-alpha-hydroxybenzenepropanoate;(alphaR,betaS)-beta-(Benzoylamino)-alpha-hydroxybenzenepropanoic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(acetyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-12-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-5-oxo-7,1;4,10beta-bis(acetyloxy)-13alpha-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1,7beta-dihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl (2E)-2-methylbut-2-enoate;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-12-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)-;InChI=1/C45H53NO14/c1-9-23(2)40(53)59-38-36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32-24(3)29(21-45(38,55)42(32,6)7)58-41(54)34(50)33(27-16-12-10-13-17-27)46-39(52)28-18-14-11-15-19-28/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(

Chemical Property of Isocephalomannine

Chemical Property:

• Melting Point: 232℃ (Decomposition)
• Boiling Point: 927.4±65.0 °C(Predicted)
• PKA: 11.90±0.20(Predicted)
• PSA: 224.78000
• Density: 1.36±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 3.96290
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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:

98%min ^*data from raw suppliers

IsoCephalomannine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)OC1C2C(C(CC3C2(CO3)OC(=O)C)O)(C(=O)C(C4=C(C(CC1(C4(C)C)O)OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)C)OC(=O)C)C
• Isomeric SMILES: C/C=C(\C)/C(=O)O[C@H]1[C@H]2[C@@]([C@H](C[C@@H]3[C@]2(CO3)OC(=O)C)O)(C(=O)[C@@H](C4=C([C@H](C[C@@]1(C4(C)C)O)OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)C)OC(=O)C)C
• Uses: Iso Cephalomannine is a Cephalomannine (C258500) isomer as an impurity in Paclitaxel (P132500) active pharmaceutical ingredient. Paclitaxel impurity A. Iso Cephalomannine is a Cephalomannine (C258500) isomer as an impurity in Paclitaxel (P132500) active pharmaceutical ingredient. Paclitaxel impurity A. It binds to the N-terminal 31 amino acids of the beta-tubulin subunit in the microtubule, rather than to tubulin dimers. Paclitaxel - impurity A.

Technology Process of Isocephalomannine

There total 4 articles about Isocephalomannine 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: 78.6%

C57H81NO14Si2 → 2-debenzoyl-2-tigloyl paclitaxel (173101-54-7)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; at 20 ℃; for 1.5h;

Reference yield:

taxol (33069-62-4) → 2-debenzoyl-2-tigloyl paclitaxel (173101-54-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2-methylimidazole / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 1 h / -15 °C

3.1: thionyl chloride / dichloromethane / 1 h / 40 °C

3.2: 0.33 h / 0 °C

4.1: hydrogenchloride / acetonitrile; water / 1.5 h / 20 °C

With hydrogenchloride; thionyl chloride; 2-methylimidazole; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

1-hydroxy-7β-triethylsilyloxy-9-oxo-10β-acetyloxy-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-benzoylamino-2-triethylsilyloxy-3-phenylpropanoate] (135365-62-7) → 2-debenzoyl-2-tigloyl paclitaxel (173101-54-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 1 h / -15 °C

2.1: thionyl chloride / dichloromethane / 1 h / 40 °C

2.2: 0.33 h / 0 °C

3.1: hydrogenchloride / acetonitrile; water / 1.5 h / 20 °C

With hydrogenchloride; thionyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; water; acetonitrile;

upstream raw materials:

Tiglic acid

2'-(tert-butyldimethylsilyl)-2-debenzoyl-7-(triethylsilyl)paclitaxel

taxol

1-hydroxy-7β-triethylsilyloxy-9-oxo-10β-acetyloxy-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-benzoylamino-2-triethylsilyloxy-3-phenylpropanoate]