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Cas Database

Name	Maytansine	EINECS	252-754-7
CAS No.	35846-53-8	Density	1.32g/cm³
PSA	156.47000	LogP	3.92820
Solubility	N/A	Melting Point	183.5-184℃
Formula	C34H46 Cl N3 O10	Boiling Point	895.1°Cat760mmHg
Molecular Weight	692.206	Flash Point	495.1°C
Transport Information	N/A	Appearance	N/A
Safety	A deadly poison by intraperitoneal and intravenous routes. Moderately toxic by subcutaneous route. Human systemic effects by intravenous route: hallucinations, distorted perceptions, change in motor activity, and nausea or vomiting. An experimental teratogen. Mutation data reported. Used as an antineoplastic agent. When heated to decomposition it emits very toxic fumes of Cl⁻ and NO_x.	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	L-Alanine, N-acetyl-N-methyl-,11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-ylester, [1S-(1R,2S,3R,5R,6R,16E,18E,20S,21R)]-;Maitansine;Maysanine;Maytansin;N-Acetyl-N-methyl-L-alanine [1S-(1R,2S,3R,5R,6R,16E,18E,20S,21R)]-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-ylester;NSC 153858;	Article Data	3

Maytansine Synthetic route

: 64817-73-8
maytansine 9-O-methyl ether

: 35846-53-8
maytansine

Conditions

Conditions	Yield
With pyridine hydrochloride In tetrahydrofuran at 25℃; for 14h;	95%

: 75340-67-9
4-deoxymaytansinol

: 35846-53-8
maytansine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 2: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 3: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 4: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme

: 75349-70-1
(3E,5E,14E)-(7R,8S,12S,13S,16S)-21-Chloro-16-hydroxy-7,8,22-trimethoxy-3,13,15,19-tetramethyl-11-oxa-9,19-diaza-tricyclo[18.3.1.18,12]pentacosa-1(24),3,5,14,20,22-hexaene-10,18-dione

: 35846-53-8
maytansine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 2: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 3: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme

: 75340-66-8
C36H56ClNO5S2Si

: 35846-53-8
maytansine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h 2: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C 3: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 4: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 5: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 6: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 7: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h
2: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C
3: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C
4: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C
5: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C
6: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C
7: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C
View Scheme

: 75349-69-8
3-O-(tert-butyldimethylsilyl)-4,5-deoxymaytansinol

: 35846-53-8
maytansine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 2: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 3: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 4: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 5: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C
2: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C
3: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C
4: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C
5: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C
View Scheme

: 75349-68-7
C37H57ClN2O6S2Si

: 35846-53-8
maytansine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C 2: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 3: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 4: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 5: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 6: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C
2: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C
3: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C
4: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C
5: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C
6: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C
View Scheme

: C40H64ClNO6S2Si

: 35846-53-8
maytansine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1.) 2-propanethiol, boron trifluoride etherate, 2.) silver nitrate, aq. 2,6-lutidine / 1.) methylene chloride, - 78 deg C, 5 min, 2.) THF, 25 deg C, 1.75 h 2: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h 3: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C 4: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 5: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 6: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 7: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 8: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 1.) 2-propanethiol, boron trifluoride etherate, 2.) silver nitrate, aq. 2,6-lutidine / 1.) methylene chloride, - 78 deg C, 5 min, 2.) THF, 25 deg C, 1.75 h
2: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h
3: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C
4: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C
5: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C
6: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C
7: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C
8: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C
View Scheme

: (E)-(3S,6S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-8-{2-[(2E,4E)-(R)-6-(4-chloro-3-methoxy-5-methylamino-phenyl)-1-methoxy-5-methyl-hexa-2,4-dienyl]-[1,3]dithian-2-yl}-7-(2-methoxy-propoxy)-4,6-dimethyl-oct-4-enoatetetrabutyl-ammonium;

: 35846-53-8
maytansine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 71 percent / mesitylenesulfonyl chloride, diisopropylethylamine / benzene / 28 h / 40 °C 2: 1.) 2-propanethiol, boron trifluoride etherate, 2.) silver nitrate, aq. 2,6-lutidine / 1.) methylene chloride, - 78 deg C, 5 min, 2.) THF, 25 deg C, 1.75 h 3: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h 4: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C 5: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 6: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 7: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 8: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 9: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 71 percent / mesitylenesulfonyl chloride, diisopropylethylamine / benzene / 28 h / 40 °C
2: 1.) 2-propanethiol, boron trifluoride etherate, 2.) silver nitrate, aq. 2,6-lutidine / 1.) methylene chloride, - 78 deg C, 5 min, 2.) THF, 25 deg C, 1.75 h
3: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h
4: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C
5: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C
6: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C
7: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C
8: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C
9: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C
View Scheme

: 75340-68-0, 93221-25-1, 109764-37-6
(-)-maytansinol

: 35846-53-8
maytansine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 2: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme

: 67-56-1
methanol

: 35846-53-8
maytansine

: 64817-73-8
(3E,5E,7R,84Ξ,86S)-12c-(N-acetyl-N-methyl-L-alanyloxy)-14-chloro-10t,11c-epoxy-15,7r,84-trimethoxy-3,9c,11t,15-tetramethyl-15-aza-1(1,3)-benzena-8(4,6)-[1,3]oxazinana-cyclopentadecaphane-3,5-diene-82,14-dione

Conditions

Conditions	Yield
With trifluoroacetic acid In benzene Ambient temperature;

Maytansine History

in 1972，Maytansine was first isolated from the African plant, Maytenus ovatus (Celastraceae), later renamed Maytenus serrata,by Kupchan and co-workers in a yield of 0.2 mg/kg of dried plant material.

Maytansine Specification

Maytansine, with the CAS NO. 35846-53-8, is also called Maitansine; Maysanine; Maytansin. Maytansine is an ansamycin antibiotic originally isolated from the Ethiopian shrub Maytenus serrata. Maytansine binds to tubulin at the rhizoxin binding site, thereby inhibiting microtubule assembly, inducing microtubule disassembly, and disrupting mitosis.

Physical properties about Maytansine are: (1)ACD/LogP: 4.066; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 4.07; (4)ACD/LogD (pH 7.4): 4.07; (5)ACD/BCF (pH 5.5): 724.76; (6)ACD/BCF (pH 7.4): 722.57; (7)ACD/KOC (pH 5.5): 3880.82; (8)ACD/KOC (pH 7.4): 3869.11; (9)#H bond acceptors: 13; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.59 ; (13)Molar Refractivity: 176.691 cm³; (14)Molar Volume: 523.775 cm³; (15)Polarizability: 70.046 10-24cm³; (16)Surface Tension: 57.5769996643066 dyne/cm; (17)Density: 1.322 g/cm³; (18)Flash Point: 495.133 °C; (19)Enthalpy of Vaporization: 136.306 kJ/mol; (20)Boiling Point: 895.091 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10-,18-11+/t19-,20+,25+,26-,27-,30-,33+,34+/m1/s1;
(2)InChIKey=WKPWGQKGSOKKOO-AQPVFDFWSA-N;
(3)SmilesC[C@@H]1[C@@H]2C[C@]([C@@H](/C=C\C=C(\Cc3cc(c(c(c3)OC)Cl)N(C(=O)C[C@H]([C@]4([C@@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)/C)OC)(NC(=O)O2)O;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
human	TDLo	intravenous	190ug/kg/5D (.19mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Journal of the National Cancer Institute. Vol. 60, Pg. 93, 1978.
mouse	LD50	intraperitoneal	245ug/kg (.245mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse	LD50	intravenous	1530ug/kg (1.53mg/kg)	BLOOD: THROMBOCYTOPENIA BLOOD: LEUKOPENIA SKIN AND APPENDAGES (SKIN): HAIR: OTHER	National Technical Information Service. Vol. PB82-165507,
rat	LD50	subcutaneous	480ug/kg (.48mg/kg)		Cancer Treatment Reports. Vol. 61, Pg. 1333, 1977.
rat	LD50	subcutaneous	480ug/kg (.48mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Cancer Treatment Reports. Vol. 61, Pg. 1333, 1977.

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