N²'-deacetyl-N²'-[3-[[1-[[4-[[[(1S)-5-amino-1-carboxypentyl]amino]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-1-oxopropyl]maytansine

Base Information

• Chemical Name: N²'-deacetyl-N²'-[3-[[1-[[4-[[[(1S)-5-amino-1-carboxypentyl]amino]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-1-oxopropyl]maytansine
• CAS No.: 1281816-04-3
• Molecular Formula: C₅₃H₇₅ClN₆O₁₅S
• Molecular Weight: 1103.73
• Mol file: 1281816-04-3.mol

Synonyms:

Chemical Property of N²'-deacetyl-N²'-[3-[[1-[[4-[[[(1S)-5-amino-1-carboxypentyl]amino]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-1-oxopropyl]maytansine

Chemical Property:

Purity/Quality:

99%+, ^*data from raw suppliers

Lys-SMCC-DM1(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Lys-SMCC-DM1 is designed to eradicate cancer cells that express the target antigen on their cell surface.

Technology Process of N²'-deacetyl-N²'-[3-[[1-[[4-[[[(1S)-5-amino-1-carboxypentyl]amino]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-1-oxopropyl]maytansine

There total 7 articles about N²'-deacetyl-N²'-[3-[[1-[[4-[[[(1S)-5-amino-1-carboxypentyl]amino]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-1-oxopropyl]maytansine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

N-succinimidyl 4-(N-maleimidomethyl) trans-cyclohexane-1-carboxylate + N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)maytansine (139504-50-0) + L-lysine (56-87-1,3506-25-0) → N2'-deacetyl-N2'-[3-[[1-[[4-[[[(1S)-5-amino-1-carboxypentyl]amino]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-1-oxopropyl]maytansine (1281816-04-3)

Guidance literature:

In aq. phosphate buffer; N,N-dimethyl acetamide; at 20 ℃; for 2h; pH=7.4; Inert atmosphere;

DOI:10.1021/mp5007757

Reference yield:

L-lysine (56-87-1,3506-25-0) + SMCC-MDC (1228105-51-8) → lysine-MCC-DM1 (1281816-04-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

Reference yield:

Fmoc-N-Me-L-Ala-maytansinol (1452404-52-2) → lysine-MCC-DM1 (1281816-04-3)

Guidance literature:

Multi-step reaction with 3 steps

1: piperidine / acetonitrile / 4 h / 20 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

With piperidine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

Fmoc-N-Me-L-Ala-maytansinol

(1⁴S,1⁶S,3²R,3³R,2R,4S,10E,12E,14R)-8⁶-chloro-1⁴-hydroxy-8⁵,14-dimethoxy-3³,2,7,10-tetramethyl-1²,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl methyl-L-alaninate

4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester

L-lysine

Refernces

• 1、 -. "COMPOUNDS AND METHODS FOR THE TREATMENT OF EGFR POSITIVE DISEASES". . . Retrieved 2014/07/08.
• 2、 -. "MAYTANSINOID DERIVATIVES". . . Retrieved 2014/07/08.