Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside

Base Information

• Chemical Name: Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside
• CAS No.: 128643-86-7
• Molecular Formula: C₅₁H₅₈O₁₀
• Molecular Weight: 831.016
• Mol file: 128643-86-7.mol

Synonyms:Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside

Chemical Property of Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside

There total 1 articles about Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-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:

Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside (128643-85-6) + benzyl chloride (100-44-7) → Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside (128643-86-7)

Guidance literature:

With potassium hydroxide; Yield given. Multistep reaction; 1) 1,4-dioxane, 80 deg C, 2) heating, 4 h;

DOI:10.1016/0008-6215(90)84108-7

Reference yield: 64.0%

Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside (128643-86-7) → methyl [2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (90164-78-6)

Guidance literature:

With selenium(IV) oxide; acetic acid; In 1,4-dioxane; for 0.666667h; Heating;

DOI:10.1016/0008-6215(90)84108-7

Reference yield:

Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside (128643-86-7) → Methyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside (128643-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / acetic acid, SeO₂ / dioxane / 0.67 h / Heating

2: 69 percent / CuBr₂, tetraethylammonium bromide, silver triflate, molecular sieves 4 Angstroem / CH₂Cl₂; dimethylformamide / 16 h / Ambient temperature

With selenium(IV) oxide; 4 A molecular sieve; tetraethylammonium bromide; silver trifluoromethanesulfonate; acetic acid; copper(ll) bromide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84108-7

upstream raw materials:

Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside

benzyl chloride

Downstream raw materials:

methyl [2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Methyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside