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CAS No.: | 57103-68-1 |
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Name: | Maytansine, O3-de2-(acetylmethylamino)-1-oxopropyl- |
Article Data: | 16 |
Molecular Structure: | |
Formula: | C28H37 Cl N2 O8 |
Molecular Weight: | 565.063 |
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 |
Density: | 1.34g/cm3 |
Melting Point: | 205-207℃ |
Boiling Point: | 835.8°Cat760mmHg |
Flash Point: | 459.3°C |
PSA: | 130.09000 |
LogP: | 3.51050 |
ansamitocin P-3
maytansinol
Conditions | Yield |
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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; |
maytanbutine
maytansinol
Conditions | Yield |
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With lithium aluminium tetrahydride In tetrahydrofuran at -23℃; for 3h; |
(-)-maytansinol
maytansinol
Conditions | Yield |
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hydrolysis; |
4-deoxymaytansinol
maytansinol
Conditions | Yield |
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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 View Scheme |
(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
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 View Scheme |
C36H56ClNO5S2Si
maytansinol
Conditions | Yield |
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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 View Scheme |
3-O-(tert-butyldimethylsilyl)-4,5-deoxymaytansinol
maytansinol
Conditions | Yield |
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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 View Scheme |
C37H57ClN2O6S2Si
maytansinol
Conditions | Yield |
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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 View Scheme |
maytansinol
Conditions | Yield |
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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 View Scheme |
maytansinol
Conditions | Yield |
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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 View Scheme |