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

Base Information

• Chemical Name: 2-Hydroxy-3,17|A-O-bis(methoxymethyl)estradiol
• CAS No.: 217792-89-7
• Molecular Formula: C22H32 O5
• Molecular Weight: 376.493
• DSSTox Substance ID: DTXSID20441259
• Wikidata: Q82257954
• Mol file: 217792-89-7.mol

Synonyms:217792-89-7;2-Hydroxy-3,17|A-O-bis(methoxymethyl)estradiol;2-Hydroxy-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]phenanthren-2-ol;2-Hydroxy-3,17?-O-bis(methoxymethyl)estradiol;SCHEMBL6744803;DTXSID20441259;2-Hydroxy-3,17 beta -O-bis(methoxymethyl)estradiol;J-014284

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.561
• Boiling Point: 494.374°C at 760 mmHg
• PKA: 9.52±0.60(Predicted)
• Flash Point: 252.788°C
• PSA: 57.15000
• Density: 1.182g/cm³
• LogP: 4.22010
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 376.22497412
• Heavy Atom Count: 27
• Complexity: 499

Purity/Quality:

97% ^*data from raw suppliers

2-Hydroxy-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)O)OCOC
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OCOC)CCC4=CC(=C(C=C34)O)OCOC
• Uses: 2-Hydroxy-3,17β-O-bis(methoxymethyl)estradiol (cas# 217792-89-7) is a compound useful in organic synthesis.

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

There total 5 articles about 2-Hydroxy-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: 95.0%

(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) → (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 (217792-89-7)

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 2h;

With Trimethyl borate; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; for 5h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; cyclohexane; at 20 ℃; for 8h;

DOI:10.1021/jm049647a

Reference yield: 86.0%

(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-2-carbaldehyde (123715-80-0) → (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]phenanthren-2-ol (217792-89-7)

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-2-carbaldehyde; With sodium phosphate dibasic dihydrate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 24h;

With sodium hydroxide; In methanol; at 20 ℃; for 2h;

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]phenanthren-2-ol (217792-89-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93.7 percent / diisopropylethylamine / tetrahydrofuran / 24 h / 50 - 55 °C

2.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C

2.2: trimethylborate / tetrahydrofuran; cyclohexane / -78 - 0 °C

2.3: 65.2 percent / sodium perborate tetrahydrate / H₂O; ethyl acetate

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

DOI:10.1002/jlcr.1131

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-2-carbaldehyde

(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

estradiol

2-formylestradiol

Downstream raw materials:

2-methoxyestradiol 3,17-O,O-bis-sulfamate

(17β)-2-benzyloxy-1,3,5(10)-estratriene-3,17-diol

2-hydroxyestradiol-3,17β-O,O-bis(N-trityl)sulfamate

2-O-benzyloxyestradiol-3,17β-O,O-bis(N-trutyl)sulfamate

Refernces

• 1、 Wang, Min,Xu, Lu,Gao, Mingzhang,Miller, Kathy D.,Sledge, George W.,Zheng, Qi-Huang. "Synthesis of 2-[11C]methoxy-3,17β-O,O-bis(sulfamoyl) estradiol as a new potential PET agent for imaging of steroid sulfatase (STS) in cancers". scheme or table. p. 864 - 870. Retrieved 2012/07/14.
• 2、 Kang, Choong Mo,Choe, Yearn Seong,Jung, Kyung-Ho,Choi, Joon Young,Lee, Kyung-Han,Kim, Byung-Tae. "Synthesis and in vitro evaluation of 2-[11C]methoxyestradiol-3, 17β-O,O-bissulfamate for in vivo studies of angiogenesis". experimental part. p. 783 - 787. Retrieved 2012/05/20.