benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-β-D-glucopyranoside
• CAS No.: 121256-10-8
• Molecular Formula: C₂₇H₃₆O₁₂
• Molecular Weight: 552.576
• Mol file: 121256-10-8.mol

Synonyms:benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-β-D-glucopyranoside

Chemical Property of benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-β-D-glucopyranoside

There total 4 articles about benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-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: 74.0%

benzyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside (18404-72-3) + p-methoxybenzyl chloride (824-94-2) → benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-β-D-glucopyranoside (121256-10-8)

Guidance literature:

benzyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside; With di(n-butyl)tin oxide; In methanol; Heating;

p-methoxybenzyl chloride; With tetra-(n-butyl)ammonium iodide; In toluene; at 70 ℃;

DOI:10.1016/j.bmcl.2006.01.040

Reference yield:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (67310-53-6) → benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-β-D-glucopyranoside (121256-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / NaOMe; MeOH

2.1: Bu₂SnO / methanol / Heating

2.2: 74 percent / TBAI / toluene / 70 °C

With methanol; sodium methylate; di(n-butyl)tin oxide; In methanol;

DOI:10.1016/j.bmcl.2006.01.040

Reference yield:

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-60-8,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4) → benzyl 4-O-[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-β-D-glucopyranoside (121256-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere; Molecular sieve

2.1: sodium methylate / methanol / Inert atmosphere

3.1: di(n-butyl)tin oxide / methanol / 8 h / Reflux; Inert atmosphere

3.2: 8 h / Molecular sieve; Inert atmosphere; Reflux

With boron trifluoride diethyl etherate; sodium methylate; di(n-butyl)tin oxide; In methanol; dichloromethane;

DOI:10.1021/acs.joc.6b00478

upstream raw materials:

benzyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside

p-methoxybenzyl chloride

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose