methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside

Base Information

• Chemical Name: methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside
• CAS No.: 90633-88-8
• Molecular Formula: C₂₉H₃₂O₇
• Molecular Weight: 492.569
• Mol file: 90633-88-8.mol

Synonyms:methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside

Chemical Property of methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside

There total 16 articles about methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-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: 100.0%

benzyl bromide (100-39-0) + methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside (162680-20-8) → methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside (90633-88-8)

Guidance literature:

methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.166667h;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 1.5h;

DOI:10.1039/c8ob02225a

Reference yield: 89.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5) → methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside (90633-88-8)

Guidance literature:

With 3,4-bis((3,5-bis(trifluoromethyl)phenyl)amino)cyclobut-3-ene-1,2-dione; In dichloromethane; at 20 ℃; for 0.42h; Solvent; Time; Inert atmosphere;

DOI:10.1002/ejoc.201301116

Reference yield: 83.0%

methanol (67-56-1) + methyl 2,3-di-O-benzyl-4,6-O-(p-chlorobenzylidene)-α-D-glucopyranoside → methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside (90633-88-8)

Guidance literature:

With di-tert-butyl (2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1‘-biphenyl]-2-yl)phosphine; methanesulfonato(2-(di-tert-butylphosphino)-3-methoxy-6-methyl-2′,4′,6′-tri-isopropyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)palladium(II); sodium t-butanolate; In 1,4-dioxane; at 50 ℃; for 22.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02672

upstream raw materials:

methanol

p-Anisaldehyde dimethyl acetal

methyl-alpha-D-glucopyranoside

1,5-anhydro-2,3-di-O-benzyl-1-hydrazi-4,6-O-(4-methoxybenzylidene)-D-glucitol

Downstream raw materials:

methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside

C₂₅H₃₀O₆

C₂₅H₂₈O₆

C₂₄H₂₆O₆