ChemicalBook CAS DataBase List Mertansine

Mertansine synthesis

4synthesis methods

Product Name:Mertansine
CAS Number:139504-50-0
Molecular formula:C35H48ClN3O10S
Molecular Weight:738.29

Methenol DM1 is a tubulin inhibitor that binds to the end of microtubules and inhibits microtubule dynamics. N2'-deacetyl-N2'-(3-Mercapto-1-oxopropyl)-Maytansine can be synthesized by multi-step reactions with 2 steps: First: 32%/dicyclohexylcarbodiimide; ZnCl2/CH2Cl2; diethyl ether/2h/20 °C; Second: 76% dithiothreitol; EDTA/methanol; ethyl acetate; aq. phosphate buffer/3h/pH 7.5.

138148-68-2
48 suppliers
$35.00/1mg

139504-50-0
201 suppliers
$66.00/2mg

Yield:139504-50-0 4.1 g

Reaction Conditions:

with 1,4-dithio-L-threitol in methanol;ethyl acetate at 20; for 3.5 h;Inert atmosphere;

Steps:

1.4 Step (4)
The crude compound DM1-3L (5g) and DL-dithiothreitol (5.1g) were mixed and dissolved with ethyl acetate (120ml) and methanol (120ml), and phosphate buffer (120mM, pH=7.5, 120ml) was added, Under argon protection, react at room temperature for 3.5 hours, add phosphate buffer (pH=6.0, 240ml), extract with ethyl acetate, wash the organic phase with water, concentrate under reduced pressure to dryness, and separate by column chromatography to obtain compound DM1 (4.1g) ).

References:

Shanghai Pharmaceutical Group Co., Ltd.;Xia Guangbing;Zhu Yang;Zhou Wei;Yao Junliang;Yao Changliang;Liu Junyao;Xia Guangxin;Liu Yanjun CN111978332, 2020, A Location in patent:Paragraph 0074; 0085-0106

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57103-68-1 Synthesis