3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside

Base Information

• Chemical Name: 3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside
• CAS No.: 253790-76-0
• Molecular Formula: C₅₇H₆₀O₁₅
• Molecular Weight: 985.094
• Mol file: 253790-76-0.mol

Synonyms:3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside

Chemical Property of 3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside

There total 12 articles about 3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside 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: 49.0%

3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside (253790-75-9) → 3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside (253790-76-0)

Guidance literature:

With methylamine; In methanol; dichloromethane; at -20 ℃; for 9h;

DOI:10.1021/jo9906983

Reference yield:

2-<3,4-bis(benzyloxy)phenyl>ethanol (96826-11-8) → 3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside (253790-76-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / silver carbonate; molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 20 °C

2: 94 percent / sodium methoxide / methanol / 2 h / 20 °C

3: 86 percent / pyridine / 0 - 20 °C

4: 92 percent / pyridine / 0 - 20 °C

5: 79 percent / AcOH / dioxane / 6 h / 110 °C

6: 79 percent / DCC; DMAP; DMAP*HCl / CH₂Cl₂ / Heating

7: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C

8: 73 percent / boron trifluoride diethyl etherate / CH₂Cl₂ / 5 h / -20 °C

9: 49 percent / methylamine / CH₂Cl₂; methanol / 9 h / -20 °C

With pyridine; dmap; selenium(IV) oxide; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; silver carbonate; methylamine; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; 1: glycosylation; ortho-esterification / 2: Deacetylation / 3: tritylation / 4: Acetylation / 5: Rearrangement / 6: Esterification / 7: Oxidation / 8: rhamnosylation / 9: Deacetylation;

DOI:10.1021/jo9906983

Reference yield:

(E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid (54429-62-8) → 3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside (253790-76-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / DCC; DMAP; DMAP*HCl / CH₂Cl₂ / Heating

2: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C

3: 73 percent / boron trifluoride diethyl etherate / CH₂Cl₂ / 5 h / -20 °C

4: 49 percent / methylamine / CH₂Cl₂; methanol / 9 h / -20 °C

With dmap; selenium(IV) oxide; boron trifluoride diethyl etherate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; methylamine; In 1,4-dioxane; methanol; dichloromethane; 1: Esterification / 2: Oxidation / 3: rhamnosylation / 4: Deacetylation;

DOI:10.1021/jo9906983

upstream raw materials:

3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside

2-<3,4-bis(benzyloxy)phenyl>ethanol

(E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside

Downstream raw materials:

Acteoside

Refernces