methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside
• CAS No.: 474382-55-3
• Molecular Formula: C₅₅H₅₈O₁₁
• Molecular Weight: 895.059
• Mol file: 474382-55-3.mol

Synonyms:methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property of methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside

There total 11 articles about methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-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: 76.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) + methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside (76419-48-2) → methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside + methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside (474382-55-3)

Guidance literature:

With gold(III) chloride; In dichloromethane; at -60 ℃; for 0.5h; diastereoselective reaction; Molecular sieve; Inert atmosphere; Schlenk technique; Darkness;

DOI:10.1021/jacs.5b07895

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) + 2,3,4,6-tetra-O-benzyl N-(phenyl)-trifluoroacetimidate → methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside + methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside (474382-55-3)

Guidance literature:

With MS 4 Angstroem AW 300; ytterbium(III) triflate; In 1,4-dioxane; diethyl ether; toluene; at -10 ℃; for 1h;

DOI:10.1016/S0040-4039(02)01124-3

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside (474382-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaH / CH₂Cl₂ / 2 h / 0 °C

2: MS 4 Angstroem AW 300 / Yb(OTf)3 / toluene; diethyl ether; dioxane / 1 h / -10 °C

With MS 4 Angstroem AW 300; sodium hydride; ytterbium(III) triflate; In 1,4-dioxane; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4039(02)01124-3

upstream raw materials:

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl diethyl phosphite

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

methyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-α-D-glucopyranoside