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71610-00-9 Usage

Chemical Properties

Off-White Solid

Occurrence

A taxane derivative, cephalomannine occurs in the extract of Cephalotaxus rnannii. It has been obtained as colourless needles from MeOH aq. and is laevorotatory with a specific rotation of [α]D -41° (MeOH).

Uses

Different sources of media describe the Uses of 71610-00-9 differently. You can refer to the following data:
1. 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
2. Antitumor, antiproliferative.
3. similar anti-cancer function as Taxol

Check Digit Verification of cas no

The CAS Registry Mumber 71610-00-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,6,1 and 0 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 71610-00:
(7*7)+(6*1)+(5*6)+(4*1)+(3*0)+(2*0)+(1*0)=89
89 % 10 = 9
So 71610-00-9 is a valid CAS Registry Number.

71610-00-9 Well-known Company Product Price

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  • USP

  • (1491343)  Cephalomannine  United States Pharmacopeia (USP) Reference Standard

  • 71610-00-9

  • 1491343-20MG

  • 22,183.20CNY

  • Detail
  • Sigma

  • (C4991)  Cephalomannine  ≥97% (HPLC), solid

  • 71610-00-9

  • C4991-1MG

  • 1,711.71CNY

  • Detail
  • Sigma

  • (C4991)  Cephalomannine  ≥97% (HPLC), solid

  • 71610-00-9

  • C4991-5MG

  • 5,896.80CNY

  • Detail

71610-00-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Cephalomannine

1.2 Other means of identification

Product number -
Other names CEPHALOMANNINE:BENZENEPROPANOICACID,-HYDROXY--[(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]OX...

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:71610-00-9 SDS

71610-00-9Synthetic route

C2HF3O2*C40H47NO13

C2HF3O2*C40H47NO13

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

(E)-2-methylbut-2-enoyl chloride

cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
81%
C47H52Cl3NO15
502626-21-3

C47H52Cl3NO15

cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
With ammonium acetate In tetrahydrofuran; methanol14 mg
7-trichloroacetyl-3'-debenzoylpaclitaxel
261728-77-2

7-trichloroacetyl-3'-debenzoylpaclitaxel

cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: 14 mg / ammonium acetate / methanol; tetrahydrofuran
View Scheme
C45H48Cl5NO14
204125-01-9

C45H48Cl5NO14

cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
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

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

cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
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
7-trichloroacetylbaccatin III
204124-97-0

7-trichloroacetylbaccatin III

cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
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
2'-acetylcephalomannine
861856-91-9

2'-acetylcephalomannine

cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
With methanol; dimethyl amine at 3℃; for 1.5h;
7-O-(β-xylosyl)cephalomannine

7-O-(β-xylosyl)cephalomannine

cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
With Enterobacter sp. CGMCC 2487 Microbiological reaction;
cephalomannine
71610-00-9

cephalomannine

C43H49NO15
157956-84-8

C43H49NO15

Conditions
ConditionsYield
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
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

cephalomannine
71610-00-9

cephalomannine

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

2'-(4-formyl)benzoyl cephalomannine

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide at 20℃; for 24h;95%
cephalomannine
71610-00-9

cephalomannine

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

13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III

Conditions
ConditionsYield
With formic acid; toluene-4-sulfonic acid at -8℃; for 7h;93.2%
With formic acid at 0℃; for 12h;
cephalomannine
71610-00-9

cephalomannine

10β-deacetylcephalomannine
76429-85-1

10β-deacetylcephalomannine

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 24h;88%
With dihydrogen peroxide; sodium hydrogencarbonate In tetrahydrofuran for 24h; Ambient temperature;72%
5,6-dithia-decanedioic acid
2906-60-7

5,6-dithia-decanedioic acid

cephalomannine
71610-00-9

cephalomannine

C53H65NO17S2
1201937-87-2

C53H65NO17S2

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

taxane

tin(IV) chloride
7646-78-8

tin(IV) chloride

cephalomannine
71610-00-9

cephalomannine

baccatin III
27548-93-2

baccatin III

Conditions
ConditionsYield
With sodium borohydrid In methanol; water66%
cephalomannine
71610-00-9

cephalomannine

cephalomanninediol
158059-99-5

cephalomanninediol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium acetate In water; acetone; tert-butyl alcohol at 0℃; for 1h;150 mg
cephalomannine
71610-00-9

cephalomannine

C43H49NO13

C43H49NO13

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

C43H49NO13

C43H49NO13

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

C49H63NO13Si

C49H63NO13Si

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

C49H65NO13Si
651293-91-3

C49H65NO13Si

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

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

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

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

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

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

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

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

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

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

C50H53NO16
173175-02-5

C50H53NO16

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

C50H52BrNO16
189131-33-7

C50H52BrNO16

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

C50H52ClNO16
189131-32-6

C50H52ClNO16

Conditions
ConditionsYield
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
cephalomannine
71610-00-9

cephalomannine

C50H52N2O18
189131-35-9

C50H52N2O18

Conditions
ConditionsYield
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
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

cephalomannine
71610-00-9

cephalomannine

C50H61NO16

C50H61NO16

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 12h;
With dmap In acetonitrile at 20℃; for 10h;
cephalomannine
71610-00-9

cephalomannine

C43H51NO14
223134-78-9

C43H51NO14

Conditions
ConditionsYield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -15℃;
cephalomannine
71610-00-9

cephalomannine

C45H52N2O15
863203-45-6

C45H52N2O15

Conditions
ConditionsYield
With sodium nitrite In acetic anhydride; acetic acid at 0℃; for 16h;
chloroamine-T
127-65-1

chloroamine-T

cephalomannine
71610-00-9

cephalomannine

C51H58N2O16S

C51H58N2O16S

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

71610-00-9Relevant articles and documents

Microbial hydrolysis of 7-xylosyl-10-deacetyltaxol to 10-deacetyltaxol

Wang, Kang,Wang, Tingting,Li, Jianhua,Zou, Jianhua,Chen, Yongqin,Dai, Jungui

body text, p. 250 - 255 (2011/10/12)

Enterobacter sp. CGMCC 2487, a bacterial strain isolated from the soil around a Taxus cuspidata Sieb. et Zucc. plant, was able to remove the xylosyl group from 7-xylosyltaxanes. The xylosidase of this strain was an inducible enzyme. In the bioconversion of 7-xylosyl-10-deacetyltaxol (7-XDT) to 10-deacetyltaxol (10-DT), for the purpose of enhancing the conversion efficiency, the effects of NH4+, oat xylan, temperature, pH value, cell density and substrate concentration on the bioconversion have been systematically investigated. 3.0 mM NH4+, 0.6% oat xylan in the media could enhance the yield of 10-DT; the optimum biocatalytic temperature was 26 °C and optimum pH value was 6.0. The highest conversion rate and yield of 10-DT from 7-XDT reached 92% and 764 mg/L, respectively. In addition, the biocatalytic capacity of the cell cultures remained 66.1% after continuous three batches. These results indicate that converting 7-XDT to 10-DT, a useful intermediate for the semisynthesis of paclitaxel or other taxane-based anticancer drugs by a novel bacterial strain, Enterobacter sp. CGMCC 2487, would be an alternative for the practical application in the future.

Synthesis of taxol, analogs and intermediates with variable A-nng side chains

-

Page 8-9, (2010/01/31)

An efficient protocol for the synthesis of taxol, taxol analogs, and their intermediates is described. The process includes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, calphalomanninne and various analogs, including photoaffinity labeling candidates.

A process for the production of taxol

-

, (2008/06/13)

A process has been developed for production of taxols A,B,C with high yields from 7-xylosyl-10-deacetyl taxol A (taxol analogue A or, xyloside A), 7-xylosyl-10-deacetyl-taxol B (taxol analogue B or xyloside B), 7-xylosyl-10-deacetyl-taxol C (taxol analogue C or xyloside C), which preferably comprises (i) isolating the taxol analogues A,B,C from the stembark of Taxus wallichianaby an improved process devoid of a solvent partitioning step, (ii) treating the isolated taxol analogues A,B,C with periodates in an acid free polar solvent medium to cleave the diol into dialdehyde at ambient temperature (iii) reducing the dialdehyde solution with borohydride in a polar solvent-acetic acid medium at 0-40°C into an acetal, (iv) acidifying the resultant acetal with a mixture of mineral acid-polar solvent at 0-40°C into intermediate product 10-deacetyl taxols A,B,C (v) reacting 10-deacetyl taxols A or B or C with a silane in presence of a base at 20-40°C to protect 2', 7-hydroxyl groups, of 10-deacetyl taxols A,B,C (vi) acetylating the 10-hydroxyl group in situwith an acetylating agent at 10-40°C, (vii) deprotecting the 2', 7-hydroxyl groups with a mixture of mineral acid-polar solvent at 0-10°C (viii) isolating taxols A or B or C by chromatography over silica.

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