4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside

Base Information

Chemical Name:4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside
CAS No.:683773-23-1
Molecular Formula:C₆₀H₇₄O₁₃
Molecular Weight:1003.24
Hs Code.:

Synonyms:4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside

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Chemical Property of 4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside

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Technology Process of 4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside

There total 11 articles about 4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside 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: 66.0%

: 100-39-0
benzyl bromide

: 683773-22-0
4-pentenyl 2,4-di-O-acetyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside

: 683773-23-1
4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: 4-pentenyl 2,4-di-O-acetyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside; With potassium hydroxide; In 1,4-dioxane; at 40 ℃; for 0.25h;

benzyl bromide; With sodium hydroxide; In 1,4-dioxane; at 80 ℃; for 48h;
DOI:10.1021/jo030304e

Reference yield:

: 821-09-0
n-Pent-4-enyl alcohol

: 683773-23-1
4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: p-toluenesulfonic acid monohydrate / 36 h / 95 °C

2.1: p-toluenesulfonic acid monohydrate / dimethylformamide / 2 h / 50 °C

2.2: 985 mg / pyridine / 48 h / 20 °C

3.1: 60 percent / 4 Angstroem molecular sieves; iodonium biscollidine perchlorate / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

4.1: 87 percent / thiourea; pyridine / ethanol / 1.5 h / 60 °C

5.1: 100 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / cooling

6.1: KOH / dioxane / 0.25 h / 40 °C

6.2: 66 percent / NaOH / dioxane / 48 h / 80 °C

With pyridine; potassium hydroxide; iodonium(di-γ-collidine) perchlorate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; toluene-4-sulfonic acid; thiourea; In 1,4-dioxane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo030304e

Reference yield:

: 3615-41-6,478518-52-4
L-Rhamnose

: 683773-23-1
4-pentenyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-2-O-methyl-4-O-(2,3-di-O-benzyl-4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: p-toluenesulfonic acid monohydrate / 36 h / 95 °C

2.1: p-toluenesulfonic acid monohydrate / dimethylformamide / 2 h / 50 °C

2.2: 985 mg / pyridine / 48 h / 20 °C

3.1: 60 percent / 4 Angstroem molecular sieves; iodonium biscollidine perchlorate / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

4.1: 87 percent / thiourea; pyridine / ethanol / 1.5 h / 60 °C

5.1: 100 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / cooling

6.1: KOH / dioxane / 0.25 h / 40 °C

6.2: 66 percent / NaOH / dioxane / 48 h / 80 °C

With pyridine; potassium hydroxide; iodonium(di-γ-collidine) perchlorate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; toluene-4-sulfonic acid; thiourea; In 1,4-dioxane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo030304e