b-D-Glucopyranoside,2-methoxy-4-[(1S,3aR,4R,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenyl

Base Information

• Chemical Name: b-D-Glucopyranoside,2-methoxy-4-[(1S,3aR,4R,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenyl
• CAS No.: 24404-49-7
• Molecular Formula: C₂₆H₃₂O₁₁
• Molecular Weight: 520.533
• Mol file: 24404-49-7.mol

Synonyms:Epipinoresinol,mono-b-D-glucopyranoside, (+)- (8CI); b-D-Glucopyranoside,2-methoxy-4-[tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenyl,[1S-(1a,3aa,4b,6aa)]-; 1H,3H-Furo[3,4-c]furan, b-D-glucopyranoside deriv.;Glucopyranoside, epipinoresinol, (+)-b-D- (8CI); Simplocosin

Chemical Property of b-D-Glucopyranoside,2-methoxy-4-[(1S,3aR,4R,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenyl

Chemical Property:

Purity/Quality:

≥97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of b-D-Glucopyranoside,2-methoxy-4-[(1S,3aR,4R,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenyl

There total 4 articles about b-D-Glucopyranoside,2-methoxy-4-[(1S,3aR,4R,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenyl 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:

(+)-pinoresinol 4-O-[6''-O-galloyl]-β-D-glucopyranoside (1177291-33-6) → (+)-pinoresinol O-β-D-glucopyranoside (24404-49-7,41607-20-9,74983-66-7,69251-96-3)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.phytochem.2009.07.020

Reference yield:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester (76874-00-5) → (+/-)-Pinoresinol-4'-O-β-D-monoglucoside (24404-49-7,41607-20-9,69251-96-3,74983-66-7)

Guidance literature:

With sodium methylate; In methanol; Yield given; Ambient temperature; pH 10;

DOI:10.1016/S0031-9422(00)98258-X

Reference yield:

coniferal alcohol (458-35-5,32811-40-8,69056-21-9) → (+/-)-Pinoresinol-4'-O-β-D-monoglucoside (24404-49-7,41607-20-9,69251-96-3,74983-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 12 percent / CuSO₄, air / H₂O; methanol / 20 h / 25 °C / Irradiation

2: 2.5 percent KOH / acetone / 1.) 0 deg C, 1.5 h, 2.) 5 deg C, overnight

3: 1 M NaOMe / methanol / Ambient temperature; pH 10

With potassium hydroxide; air; sodium methylate; copper(II) sulfate; In methanol; water; acetone;

DOI:10.1016/S0031-9422(00)98258-X

upstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester

coniferal alcohol

(+/-)-pinoresinol

(+)-pinoresinol 4-O-[6''-O-galloyl]-β-D-glucopyranoside

Downstream raw materials:

(3R,4S,5S,6R)-2-{4-[(1S,3aR,4S,6aR)-4-(3,4-Dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2-methoxy-phenoxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

pinoresinol

(+)-pinoresinol monomethyl ether

D-Glucose

Refernces

• 1、 Vermes, Barbara,Seligmann, Otto,Wagner, Hildebert. "SYNTHESIS OF BIOLOGICALLY ACTIVE TETRAHYDROFUROFURANLIGNAN-(SYRINGIN, PINORESINOL)- MONO- AND BIS-GLYCOSIDES". . p. 3087 - 3090. Retrieved 2007/10/02.