Duocarmycin sa

Base Information

• Chemical Name: Duocarmycin sa
• CAS No.: 130288-24-3
• Molecular Formula: C25H23 N3 O7
• Molecular Weight: 477.474
• DSSTox Substance ID: DTXSID30926663
• Nikkaji Number: J594.868A
• Wikidata: Q72470566
• Metabolomics Workbench ID: 105744
• ChEMBL ID: CHEMBL308086
• Mol file: 130288-24-3.mol

Synonyms:(+)-duocarmycin SA;Cyclopropa(c)pyrrolo(3,2-e)indole-6-carboxylic acid, 1,2,4,5,8,8a-hexahydro-4-oxo-2-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester, (7bR)-;duocarmycin SA

Chemical Property of Duocarmycin sa

Chemical Property:

• Vapor Pressure: 8.82E-25mmHg at 25°C
• Boiling Point: 787.7°Cat760mmHg
• PKA: 13.12±0.20(Predicted)
• Flash Point: 430.2°C
• PSA: 122.95000
• Density: 1.53g/cm³
• LogP: 2.74020
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 477.15360008
• Heavy Atom Count: 35
• Complexity: 971

Purity/Quality:

99% ^*data from raw suppliers

DuocarmycinSA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C2C(=C1)C=C(N2)C(=O)N3CC4CC45C3=CC(=O)C6=C5C=C(N6)C(=O)OC)OC)OC
• Isomeric SMILES: COC1=C(C(=C2C(=C1)C=C(N2)C(=O)N3C[C@H]4C[C@@]45C3=CC(=O)C6=C5C=C(N6)C(=O)OC)OC)OC
• Uses: Duocarmycin SA is an antitumor antibiotic.

Technology Process of Duocarmycin sa

There total 113 articles about Duocarmycin sa 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: 94.0%

methyl (S)-4-hydroxy-8-(hydroxymethyl)-6-(5,6,7-trimethoxy-1Hindole-2-carbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate → (+)-duocarmycin SA (130288-24-3)

Guidance literature:

With tributylphosphine; azodicarbonyl dimorpholide; In tetrahydrofuran; for 2h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.8b00285

Reference yield: 92.0%

(8S)-4-hydroxy-8-methanesulfonyloxymethyl-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carboxylic acid methyl ester → (+)-duocarmycin SA (130288-24-3)

Guidance literature:

With caesium carbonate; In acetonitrile; at 23 ℃; for 1h;

DOI:10.1021/ja035303i

Reference yield: 91.0%

duocarmycin (144667-38-9,152785-82-5) → (+)-duocarmycin SA (130288-24-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1016/S0040-4039(97)01716-4

upstream raw materials:

duocarmycin

(R)-8-Chloromethyl-4-hydroxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid methyl ester

1-(5,6,7-trimethoxyindole-2-carbonyl)imidazole

(+)-(7bR,8aS)-methyl 4-oxo-1,2,4,5,8,8a-hexahydrocyclopropapyrrolo<3,2-e>indole-6-carboxylate

Downstream raw materials:

duocarmycin

4'-methoxy cinnamoyl duocarmycin SA

Refernces

• 1、 -. "ENANTIOSELECTIVE SYNTHESIS OF PYRROLOINDOLE COMPOUNDS". . . Retrieved 2018/04/17.
• 2、 Tichenor, Mark S.,Trzupek, John D.,Kastrinsky, David B.,Shiga, Futoshi,Hwang, Inkyu,Boger, Dale L.. "Asymmetric total synthesis of (+)- and ent-(-)-yatakemycin and duocarmycin SA: Evaluation of yatakemycin key partial structures and its unnatural enantiomer". . p. 15683 - 15696. Retrieved 2007/10/03.