2-Formyl-3,17|A-O-bis(methoxymethyl)estradiol

Base Information

• Chemical Name: 2-Formyl-3,17|A-O-bis(methoxymethyl)estradiol
• CAS No.: 123715-80-0
• Molecular Formula: C₂₃H₃₂O₅
• Molecular Weight: 388.504
• DSSTox Substance ID: DTXSID50450273
• Nikkaji Number: J3.004.859H
• Wikidata: Q82269907
• Mol file: 123715-80-0.mol

Synonyms:123715-80-0;2-Formyl-3,17|A-O-bis(methoxymethyl)estradiol;2-Formyl-3,17beta-O-bis(methoxymethyl)estradiol;(8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2-carbaldehyde;Estra-1,3,5(10)-triene-2-carboxaldehyde, 3,17-bis(methoxymethoxy)-, (17beta)-;DTXSID50450273;AKOS030254290;2-Formyl-3,17?-O-bis(methoxymethyl)estradiol;2-Formyl-3,17 beta -O-bis(methoxymethyl)estradiol;J-004977;(8R,9S,13S,14S,17S)-3,17-Bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde

Chemical Property of 2-Formyl-3,17|A-O-bis(methoxymethyl)estradiol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 388.22497412
• Heavy Atom Count: 28
• Complexity: 539

Purity/Quality:

97% ^*data from raw suppliers

2-Formyl-3,17β-O-bis(methoxymethyl)estradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2OCOC)CCC4=CC(=C(C=C34)C=O)OCOC
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OCOC)CCC4=CC(=C(C=C34)C=O)OCOC
• Uses: Estradiol derivative Estradiol derivative.

Technology Process of 2-Formyl-3,17|A-O-bis(methoxymethyl)estradiol

There total 6 articles about 2-Formyl-3,17|A-O-bis(methoxymethyl)estradiol 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: 87.0%

(8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene (113680-55-0) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde (123715-80-0)

Guidance literature:

(8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 2.5h;

N,N-dimethyl-formamide; In tetrahydrofuran; cyclohexane; at -78 - 23 ℃; for 3h;

DOI:10.1124/mol.61.5.1053

Reference yield: 60.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + estradiol (50-28-2) + chloromethyl methyl ether (107-30-2) → (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-4-carbaldehyde (123746-55-4) + (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde (123715-80-0)

Guidance literature:

formaldehyd; estradiol; With triethylamine; magnesium chloride; In tetrahydrofuran; Reflux;

With lithium hydroxide; In methanol;

chloromethyl methyl ether; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; regioselective reaction; Heating;

DOI:10.1016/j.tet.2011.08.005

Reference yield:

estradiol (50-28-2) → (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde (123715-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / diisopropylethylamine / tetrahydrofuran / Heating

2: 1.) s-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C to RT, overnight

With sec.-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/jm9508245

upstream raw materials:

(8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene

N,N-dimethyl-formamide

chloromethyl methyl ether

2-formylestradiol

Downstream raw materials:

(8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-ol

[2-((8R,9S,13S,14S,17S)-3,17-Bis-methoxymethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl)-ethyl]-carbamic acid benzyl ester

[3-((8R,9S,13S,14S,17S)-3,17-Bis-methoxymethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl)-propyl]-carbamic acid benzyl ester

3,17β-bis(benzyloxy)estra-1,3,5(10)-triene-2-carbaldehyde