Cephalomannine supplier | CasNO.71610-00-9

Name
Cephalomannine
EINECS
CAS No. 71610-00-9
Article Data10
CAS DataBase
Density 1.36 g/cm³
Solubility DMSO: 14 mg/mL
Melting Point 139-141oC
Formula C₄₅H₅₃NO₁₄
Boiling Point 929.5 °C at 760 mmHg
Molecular Weight 831.914
Flash Point 516 °C
Transport Information
Appearance solid
Safety 26-39
Risk Codes 37/38-41
Molecular Structure
Hazard Symbols Xi
Synonyms Benzenepropanoic acid, alpha-hydroxy-beta-((2-methyl-1-oxo-2-butenyl)amino)-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(aR*,betaS*),11alpha,12alpha,12aalpha,12balpha))-;Benzenepropanoic acid,R-hydroxy-a-[[(2E)-2- methyl-1-oxo-2-butenyl]amino]-,(2aR,4S,- 4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis- (acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,- 11,12,12a,12b-dodecahydro-4,11-dihydroxy- 4a,8,13,13-tetramethyl-5-oxo-7,11-methano- 1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester,(RR,aS)-;Benzenepropanoic acid, alpha-hydroxy-beta-(((2E)-2-methyl-1-oxo-2-butenyl)amino)-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (alphaR,betaS)-;Taxol B;
PSA 221.29000
LogP 3.77900

Synthetic route

: C2HF3O2*C40H47NO13

: 35660-94-7
(E)-2-methylbut-2-enoyl chloride

: 71610-00-9
cephalomannine

Conditions

Conditions	Yield
	81%

: 502626-21-3
C47H52Cl3NO15

: 71610-00-9
cephalomannine

Conditions

Conditions	Yield
With ammonium acetate In tetrahydrofuran; methanol	14 mg

: 261728-77-2
7-trichloroacetyl-3'-debenzoylpaclitaxel

: 71610-00-9
cephalomannine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: 14 mg / ammonium acetate / methanol; tetrahydrofuran View Scheme

: 204125-01-9
C45H48Cl5NO14

: 71610-00-9
cephalomannine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl 2: pyridine 3: 14 mg / ammonium acetate / methanol; tetrahydrofuran View Scheme

: (4S,5R)-2,2-di(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid triethylamine salt

: 71610-00-9
cephalomannine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 84 percent / DCC / toluene / 2 h / 35 °C 2: HCl 3: pyridine 4: 14 mg / ammonium acetate / methanol; tetrahydrofuran View Scheme

: 204124-97-0
7-trichloroacetylbaccatin III

: 71610-00-9
cephalomannine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 84 percent / DCC / toluene / 2 h / 35 °C 2: HCl 3: pyridine 4: 14 mg / ammonium acetate / methanol; tetrahydrofuran View Scheme

: 861856-91-9
2'-acetylcephalomannine

: 71610-00-9
cephalomannine

Conditions

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

: 7-O-(β-xylosyl)cephalomannine

: 71610-00-9
cephalomannine

Conditions

Conditions	Yield
With Enterobacter sp. CGMCC 2487 Microbiological reaction;

: 71610-00-9
cephalomannine

: 157956-84-8
C43H49NO15

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.75h;	97%
Multi-step reaction with 2 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C View Scheme

: 619-66-9
4-Carboxybenzaldehyde

: 71610-00-9
cephalomannine

: 385442-68-2
2'-(4-formyl)benzoyl cephalomannine

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 20℃; for 24h;	95%

: 71610-00-9
cephalomannine

: 133524-70-6
13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III

Conditions

Conditions	Yield
With formic acid; toluene-4-sulfonic acid at -8℃; for 7h;	93.2%
With formic acid at 0℃; for 12h;

: 71610-00-9
cephalomannine

: 76429-85-1
10β-deacetylcephalomannine

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 24h;	88%
With dihydrogen peroxide; sodium hydrogencarbonate In tetrahydrofuran for 24h; Ambient temperature;	72%

: 2906-60-7
5,6-dithia-decanedioic acid

: 71610-00-9
cephalomannine

: 1201937-87-2
C53H65NO17S2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at -20 - 15℃;	70%

: taxane

: 7646-78-8
tin(IV) chloride

: 33069-62-4
taxol

: 71610-00-9
cephalomannine

: 27548-93-2
baccatin III

Conditions

Conditions	Yield
With sodium borohydrid In methanol; water	66%

...Expand

: 71610-00-9
cephalomannine

: 158059-99-5
cephalomanninediol

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium acetate In water; acetone; tert-butyl alcohol at 0℃; for 1h;	150 mg

: 71610-00-9
cephalomannine

: C43H49NO13

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / aq. H2O2; NaHCO3 / tetrahydrofuran / 24 h / 20 °C 2: 51 percent / imidazole / dimethylformamide / 1 h / 20 °C 3: 89 percent / Cu(OAc)2*H2O; air / methanol / 24 h 4: desilylation View Scheme

: 71610-00-9
cephalomannine

: C43H49NO13

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / aq. H2O2; NaHCO3 / tetrahydrofuran / 24 h / 20 °C 2: 51 percent / imidazole / dimethylformamide / 1 h / 20 °C 3: 89 percent / Cu(OAc)2*H2O; air / methanol / 24 h 4: desilylation View Scheme

: 71610-00-9
cephalomannine

: C49H63NO13Si

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / aq. H2O2; NaHCO3 / tetrahydrofuran / 24 h / 20 °C 2: 51 percent / imidazole / dimethylformamide / 1 h / 20 °C 3: 89 percent / Cu(OAc)2*H2O; air / methanol / 24 h View Scheme

: 71610-00-9
cephalomannine

: 651293-91-3
C49H65NO13Si

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / aq. H2O2; NaHCO3 / tetrahydrofuran / 24 h / 20 °C 2: 51 percent / imidazole / dimethylformamide / 1 h / 20 °C View Scheme

: 71610-00-9
cephalomannine

: 33069-62-4
taxol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / O3 / CH2Cl2 / 0.75 h / -78 °C 2: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature 3: 91 percent / o-phenylenediamine, p-TsOH / hexane / Heating View Scheme
Multi-step reaction with 4 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C 3: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature 4: 91 percent / o-phenylenediamine, p-TsOH / hexane / Heating View Scheme

: 71610-00-9
cephalomannine

: N-debenzoyl-N-(o-chlorobenzoyl)paclitaxel

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / O3 / CH2Cl2 / 0.75 h / -78 °C 2: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature 3: o-phenylenediamine, p-TsOH / hexane / Heating View Scheme
Multi-step reaction with 4 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C 3: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature 4: o-phenylenediamine, p-TsOH / hexane / Heating View Scheme

: 71610-00-9
cephalomannine

: N-debenzoyl-N-(o-bromobenzoyl)paclitaxel

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / O3 / CH2Cl2 / 0.75 h / -78 °C 2: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature 3: o-phenylenediamine, p-TsOH / hexane / Heating View Scheme
Multi-step reaction with 4 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C 3: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature 4: o-phenylenediamine, p-TsOH / hexane / Heating View Scheme

: 71610-00-9
cephalomannine

: N-debenzoyl-N-(o-nitrobenzoyl)paclitaxel

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / O3 / CH2Cl2 / 0.75 h / -78 °C 2: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature 3: o-phenylenediamine, p-TsOH / hexane / Heating View Scheme
Multi-step reaction with 4 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C 3: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature 4: o-phenylenediamine, p-TsOH / hexane / Heating View Scheme

: 71610-00-9
cephalomannine

: 173175-02-5
C50H53NO16

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / O3 / CH2Cl2 / 0.75 h / -78 °C 2: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C 3: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature View Scheme

: 71610-00-9
cephalomannine

: 189131-33-7
C50H52BrNO16

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / O3 / CH2Cl2 / 0.75 h / -78 °C 2: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C 3: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature View Scheme

: 71610-00-9
cephalomannine

: 189131-32-6
C50H52ClNO16

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / O3 / CH2Cl2 / 0.75 h / -78 °C 2: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C 3: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature View Scheme

: 71610-00-9
cephalomannine

: 189131-35-9
C50H52N2O18

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / O3 / CH2Cl2 / 0.75 h / -78 °C 2: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 150 mg / Et4NOAc, tBuOOH, OsO4 / acetone; 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 93 percent / NaIO4 / methanol; H2O / 3 h / 25 °C 3: DCC, pyrrolidinopyridine / ethyl acetate / Ambient temperature View Scheme

: 24424-99-5
di-tert-butyl dicarbonate

: 71610-00-9
cephalomannine

: C50H61NO16

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 12h;
With dmap In acetonitrile at 20℃; for 10h;

: 71610-00-9
cephalomannine

: 223134-78-9
C43H51NO14

Conditions

Conditions	Yield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -15℃;

: 71610-00-9
cephalomannine

: 863203-45-6
C45H52N2O15

Conditions

Conditions	Yield
With sodium nitrite In acetic anhydride; acetic acid at 0℃; for 16h;

: 127-65-1
chloroamine-T

: 71610-00-9
cephalomannine

: C51H58N2O16S

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 20 - 25℃;

Cephalomannine Specification

The Cephalomannine is an organic compound with the formula C₄₅H₅₃NO₁₄. The systematic name of this chemical is (2α,5β,7β,10β,13α)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-{[(2R,3S)-2-hydroxy-3-{[(2E)-2-methylbut-2-enoyl]amino}-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl benzoate. With the CAS registry number 71610-00-9, it is also named as Taxol B. The product's categories are Alkaloids; Antineoplastic and Immunosuppressive Antibiotics Enzyme Inhibitors by Enzyme; Antibiotics by Application; Chemical Structure Class; Interferes with DNA Synthesis Antibiotics; Mechanism of Action; Penicillins and Cephalosporins (beta-Lactams).

The other characteristics of Cephalomannine can be summarized as: (1)ACD/LogP: 6.59; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 6.59; (4)ACD/LogD (pH 7.4): 6.59; (5)#H bond acceptors: 15; (6)#H bond donors: 4; (7)#Freely Rotating Bonds: 17; (8)Polar Surface Area: 179.5 Å²; (9)Index of Refraction: 1.614; (10)Molar Refractivity: 212.75 cm³; (11)Molar Volume: 609.9 cm³; (12)Surface Tension: 64.2 dyne/cm; (13)Enthalpy of Vaporization: 141.65 kJ/mol; (14)Vapour Pressure: 0 mmHg at 25°C; (15)Rotatable Bond Count: 14; (16)Tautomer Count: 6; (17)Exact Mass: 831.346605; (18)MonoIsotopic Mass: 831.346605; (19)Topological Polar Surface Area: 221; (20)Heavy Atom Count: 60; (21)Complexity: 1790.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(/C(=C/C)C)N[C@@H](c1ccccc1)[C@@H](O)C(=O)O[C@@H]4C(=C3/[C@@H](OC(=O)C)C(=O)[C@]6([C@H]([C@H](OC(=O)c2ccccc2)[C@@](O)(C3(C)C)C4)[C@@]5(OC(=O)C)[C@H](OC5)C[C@@H]6O)C)/C
2. InChI:InChI=1/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)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(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1

Product Name

Cephalomannine

Synthetic route

Cephalomannine Specification

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