2(3H)-Furanone, dihydro-3-hydroxy-3,4-bis[[3-methoxy-4-(phenylmethoxy)phenyl]methyl]-, (3S,4S)-

Base Information

• Chemical Name: 2(3H)-Furanone, dihydro-3-hydroxy-3,4-bis[[3-methoxy-4-(phenylmethoxy)phenyl]methyl]-, (3S,4S)-
• CAS No.: 124988-56-3
• Molecular Formula: C34H34O7
• Molecular Weight: 554.64
• Mol file: 124988-56-3.mol

Synonyms:

Chemical Property of 2(3H)-Furanone, dihydro-3-hydroxy-3,4-bis[[3-methoxy-4-(phenylmethoxy)phenyl]methyl]-, (3S,4S)-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2(3H)-Furanone, dihydro-3-hydroxy-3,4-bis[[3-methoxy-4-(phenylmethoxy)phenyl]methyl]-, (3S,4S)-

There total 15 articles about 2(3H)-Furanone, dihydro-3-hydroxy-3,4-bis[[3-methoxy-4-(phenylmethoxy)phenyl]methyl]-, (3S,4S)- 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: 88.0%

(2R,2'S,4'S)-2-{4-[4-(benzyloxy)-3-methoxybenzyl]-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl}-3-[4'-(benzyloxy)-3'-methoxyphenyl]propanoic acid (336101-59-8) → (2S,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide (124988-56-3)

Guidance literature:

(2R,2'S,4'S)-2-{4-[4-(benzyloxy)-3-methoxybenzyl]-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl}-3-[4'-(benzyloxy)-3'-methoxyphenyl]propanoic acid; With dimethylsulfide borane complex; In diethyl ether; for 5h; Heating;

With hydrogenchloride; In diethyl ether; for 3h; Further stages.; Heating;

DOI:10.1021/jo001547z

Reference yield: 23.0%

(3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one (111194-07-1) → (2S,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide (124988-56-3) + (2R,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide (124988-57-4)

Guidance literature:

With oxygen; lithium hexamethyldisilazane; (1,4,7,10-tetraoxacyclododecane); In benzene; for 3h; Ambient temperature;

DOI:10.1016/S0040-4039(00)99653-9

Reference yield:

(R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone (111266-03-6) → (2S,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide (124988-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / -70 °C

1.2: 47 percent / toluene; tetrahydrofuran / 0.5 h / -70 °C

2.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.5 h / -70 °C

2.2: 13 percent / oxodiperoxymolybdenum(pyridine)(HMPTA) / toluene; tetrahydrofuran / 2 h / -70 °C

With potassium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1271/bbb.60096

upstream raw materials:

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

(2R,2'S,4'S)-2-{4-[4-(benzyloxy)-3-methoxybenzyl]-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl}-3-[4'-(benzyloxy)-3'-methoxyphenyl]propanoic acid

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

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

Downstream raw materials:

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

epiwikstromol

wikstromol

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.