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

Base Information

Chemical Name: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
CAS No.:253790-75-9
Molecular Formula:C₆₇H₇₀O₂₀
Molecular Weight:1195.28
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 73.0%

: 113893-72-4
2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

: 253790-74-8
3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside

: 253790-75-9
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

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 5h;
DOI:10.1021/jo9906983

Reference yield:

: 96826-11-8
2-<3,4-bis(benzyloxy)phenyl>ethanol

: 253790-75-9
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

Guidance literature:: Multi-step reaction with 8 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

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; 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;
DOI:10.1021/jo9906983

Reference yield:

: 54429-62-8
(E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid

: 253790-75-9
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

Guidance literature:: Multi-step reaction with 3 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

With dmap; selenium(IV) oxide; boron trifluoride diethyl etherate; 4-(dimethylamino)pyridine hydrochloride; acetic acid; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; 1: Esterification / 2: Oxidation / 3: rhamnosylation;
DOI:10.1021/jo9906983