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Cas Database

57103-68-1

57103-68-1

Identification

  • Product Name:Maytansine,3-O-de[2-(acetylmethylamino)-1-oxopropyl]-

  • CAS Number: 57103-68-1

  • EINECS:

  • Molecular Weight:565.063

  • Molecular Formula: C28H37 Cl N2 O8

  • HS Code:

  • Mol File:57103-68-1.mol

Synonyms:4,24-Dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosane,maytansine deriv.; Ansamitocin P 0; Antibiotic C 15003P0; Maytansinol; NSC239386

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Safety information and MSDS view more

  • Signal Word:Danger

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Maytansinol
  • Packaging:10mg
  • Price:$ 460
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  • Product Description:Maytansinol
  • Packaging:100mg
  • Price:$ 565
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Maytansinol
  • Packaging:2.5 mg
  • Price:$ 650
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Maytansinol(AnsamitocinP-0) >98%
  • Packaging:1 g
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  • Manufacture/Brand:CSNpharm
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  • Manufacture/Brand:Crysdot
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  • Manufacture/Brand:Crysdot
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  • Manufacture/Brand:Crysdot
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Relevant articles and documentsAll total 12 Articles be found

Structural requirements for antileukemic activity among the naturally occurring and semisynthetic maytansinoids.

Kupchan,Sneden,Branfman,Howie,Rebhun,McIvor,Wang,Schnaitman

, p. 31 - 37 (1978)

In an effort to determine the structural requirements for the significant antileukemic, cytotoxic, antitubulin, and antimitotic activity exhibited by the novel ansa macrolide, maytansine (1), four new C-3 ester and six new C-9 ether homologues were synthesized. The biological activities of these compounds were assayed and compared to the activities of previously reported, naturally occurring maytansinoids. From the data, it is apparent that presence of the C-3 ester is necessary for significant activity, and variations in the ester group are not accompanied by marked changes in activity. However, elimination of the ester group, as in maytansinol (7), maysine (8), normaysine (9), and maysenine (10), results in a significant decrease in biological activity. Blockage of the C-9 carbinolamide via etherification markedly reduces antileukemic and cytotoxic activity and slightly reduces antitubulin activity but has relatively little effect on antimitotic activity against sea urchin eggs. Thus, a free carbinolamide at C-9 is advantageous for optimal activity.

-

Asai,M. et al.

, p. 1079 - 1085 (1979)

-

A highly potent maytansinoid analogue and its use as a cytotoxic therapeutic agent in gold nanoparticles for the treatment of hepatocellular carcinoma

Porter, John,Ding, Yao,Hale, Sarah J.M.,Perrins, Richard D.,Robinson, Angela,Mazanetz, Michael P.,Wu, Yubo,Ma, Yinping,Conlon, Kelly,Coulter, Tom

, (2020)

Gold nanoparticles are promising drug delivery agents with the potential to deliver chemotherapeutic agents to tumour sites. The highly cytotoxic maytansinoid tubulin inhibitor DM1 has been attached to gold nanoparticles and shows tumour growth inhibition in mouse models of hepatocellular carcinoma. Attempting to improve the stability of the gold-cytotoxin bond led to the design and synthesis of novel maytansinoids with improved potency in cell viability assays and improved in vivo tolerability compared to the DM1 analogues. These novel maytansines may also have applications in other methods of drug delivery, for example as the cytotoxic component of antibody drug conjugates.

Maytansine dechloridation compound, intermediate, preparation method of compound and application

-

Paragraph 0074-0077, (2020/12/09)

The invention discloses a maytansine dechloridation compound as shown in a formula I, an intermediate, a preparation method of the compound and an application. The invention provides the maytansine dechloridation compound as shown in the formula I. The maytansine dechloridation compound can be used as an impurity standard substance for impurity research of maytansine DM1 to establish an analysis method for maytansine DM1 quality control, and a proper method is selected to effectively remove the impurities. The quality of maytansine DM1 and even ADC drugs and the safety and effectiveness of clinical application can be improved. The invention also provides the preparation method and the intermediate of the maytansine dechloridation compound as shown in the formula I.

Uses of immunoconjugates targeting CD138

-

Page/Page column 12, (2018/11/23)

Disclosed is a method and composition for treating a disease associated with target cells expressing CD138 in a multiple dose regimen. An immunoconjugate comprising an engineered targeting antibody targeting CD138 expressing cells and an effector molecule is administered in a multiple dose regimen. The multiple dose regimen comprises at least two doses and the aggregate dose administered within an active treatment cycle is an aggregate maximum tolerable dose (AMTD) or a fraction of the AMTD. The AMTD and/or said fraction exceeds the dose resulting in dose limiting toxicity (DLT) and/or exceeds the maximum tolerable dose (MTD) when the immunoconjugate is administered as a single dose, including as part of a multiple single dose regimen within said active treatment cycle.

Uses of immunoconjugates targeting CD138

-

Sheet 2, (2016/04/20)

Disclosed are methods and treatment regimes that include the administration of immunconjugates targeting CD138 to combat diseases. The immunoconjugate is either used as the sole active ingredient, as part of a treatment regime or as part of an anticancer combination.

MAYTANSINOID ANALOGS AS ANTITUMOR AGENTS

-

Page/Page column 9, (2008/06/13)

Ansamycin analogs, including maytansinoid analogs, and their use in treating cell proliferative diseases and conditions, and in particular, for use as antitumor agents.

Process route upstream and downstream products

Process route

ansamitocin P-3
66584-72-3,93221-27-3

ansamitocin P-3

maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at -20 ℃; for 2h;
With lithium (hydro)trimethoxyaluminate;
With lithium (hydro)trimethoxyaluminate;
With lithium (hydro)trimethoxyaluminate; In tetrahydrofuran; at -40 ℃;
With lithium (hydro)trimethoxyaluminate; In tetrahydrofuran; at -40 ℃; for 1.5h; Inert atmosphere;
maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at -23 ℃; for 3h;
4-deoxymaytansinol
75340-67-9

4-deoxymaytansinol

maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
Multi-step reaction with 3 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: hydrolysis
With 2,6-dimethylpyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; toluene-4-sulfonic acid; In toluene; benzene;
(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[18.3.1.1<sup>8,12</sup>]pentacosa-1<sup>(24)</sup>,3,5,14,20,22-hexaene-10,18-dione
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

maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C
2: hydrolysis
With 2,6-dimethylpyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In toluene; benzene;
C<sub>36</sub>H<sub>56</sub>ClNO<sub>5</sub>S<sub>2</sub>Si
75340-66-8

C36H56ClNO5S2Si

maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
Multi-step reaction with 6 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: hydrolysis
With pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; ammonium hydroxide; bis(acetylacetonate)oxovanadium; hydrogen fluoride; toluene-4-sulfonic acid; calcium carbonate; mercury dichloride; In toluene; acetonitrile; benzene;
3-O-(tert-butyldimethylsilyl)-4,5-deoxymaytansinol
75349-69-8

3-O-(tert-butyldimethylsilyl)-4,5-deoxymaytansinol

maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
Multi-step reaction with 4 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: hydrolysis
With 2,6-dimethylpyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; hydrogen fluoride; toluene-4-sulfonic acid; In toluene; acetonitrile; benzene;
C<sub>37</sub>H<sub>57</sub>ClN<sub>2</sub>O<sub>6</sub>S<sub>2</sub>Si
75349-68-7

C37H57ClN2O6S2Si

maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
Multi-step reaction with 5 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: hydrolysis
With 2,6-dimethylpyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; hydrogen fluoride; toluene-4-sulfonic acid; calcium carbonate; mercury dichloride; In toluene; acetonitrile; benzene;
C<sub>40</sub>H<sub>64</sub>ClNO<sub>6</sub>S<sub>2</sub>Si

C40H64ClNO6S2Si

maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
Multi-step reaction with 7 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: hydrolysis
With pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; ammonium hydroxide; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; hydrogen fluoride; toluene-4-sulfonic acid; silver nitrate; 2-propanethiol; calcium carbonate; mercury dichloride; In toluene; acetonitrile; benzene;
(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;

(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;

maytansinol
57103-68-1

maytansinol

Conditions
Conditions Yield
Multi-step reaction with 8 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: hydrolysis
With pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; 2-mesitylenesulphonyl chloride; ammonium hydroxide; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; hydrogen fluoride; toluene-4-sulfonic acid; silver nitrate; 2-propanethiol; N-ethyl-N,N-diisopropylamine; calcium carbonate; mercury dichloride; In toluene; acetonitrile; benzene;
Conditions
Conditions Yield
hydrolysis;

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