Epinortrachelogenin

Base Information

• Chemical Name: Epinortrachelogenin
• CAS No.: 125072-69-7
• Molecular Formula: C20H22 O7
• Molecular Weight: 374.39
• DSSTox Substance ID: DTXSID501130659
• Nikkaji Number: J607.701C
• Wikidata: Q104399308
• Mol file: 125072-69-7.mol

Synonyms:Epinortrachelogenin;125072-69-7;(3R,4S)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one;DTXSID501130659;HY-N3832;AKOS040761688;FS-8005;CS-0024295;(3R,4S)-Dihydro-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone;2(3H)-Furanone, dihydro-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4S)-

Chemical Property of Epinortrachelogenin

Chemical Property:

• Melting Point: 170-172℃
• PSA: 105.45000
• LogP: 1.80430
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 374.13655304
• Heavy Atom Count: 27
• Complexity: 513

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Epinortrachelogenin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C[C@H]2COC(=O)[C@]2(CC3=CC(=C(C=C3)O)OC)O)O

Technology Process of Epinortrachelogenin

There total 31 articles about Epinortrachelogenin 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: 98.0%

(2S,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide (124988-56-3) → (-)-nortrachelogenin (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 20h;

DOI:10.1021/jo001547z

Reference yield: 85.0%

dihydro-3-hydroxy-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2,(3H)-furanone (116185-15-0,116185-17-2,124988-56-3,124988-57-4,124988-60-9,124988-61-0) → epiwikstromol (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7) + wikstromol (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 20h; under 760 Torr;

DOI:10.1021/jo00255a012

Reference yield: 85.0%

dihydro-3-hydroxy-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2,(3H)-furanone (116185-15-0,116185-17-2,124988-56-3,124988-57-4,124988-60-9,124988-61-0) → epiwikstromol (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7) + wikstromol (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 20h; under 760 Torr;

DOI:10.1021/jo00255a012

upstream raw materials:

(2S,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide

1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene

(R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone

(3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one

Downstream raw materials:

(-)-O-methyltrachelogenine

(-)-O-dimethyltrachelogenine

3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone

3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone

Refernces

• 1、 Sefkow. "Enantioselective synthesis of (-)-wikstromol using a new approach via malic acid". . p. 2343 - 2349. Retrieved 2007/10/03.
• 2、 Khamlach, Kenza,Dhal, Robert,Brown, Eric. "TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL". . p. 2221 - 2224. Retrieved 2007/10/02.