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

Base Information

• Chemical Name: methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside
• CAS No.: 311778-88-8
• Molecular Formula: C₄₁H₄₈O₁₀
• Molecular Weight: 700.826
• Mol file: 311778-88-8.mol

Synonyms:methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside

Chemical Property of methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside

There total 5 articles about methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-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: 92.0%

methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (311778-87-7) → methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside (311778-88-8)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1080/07328300008544123

Reference yield:

methyl 2,3-O-isopropylidene-α-L-rhamnoside (14133-63-2) → methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside (311778-88-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 56 percent / Tf₂O / diethyl ether / 17 h / -25 - 0 °C

3: 92 percent / TFA; H₂O / CH₂Cl₂ / 3 h / 0 °C

With pyridine; trifluoromethylsulfonic anhydride; water; trifluoroacetic acid; In diethyl ether; dichloromethane; 1: Substitution / 2: Substitution / 3: Hydrolysis;

DOI:10.1080/07328300008544123

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride (78153-79-4,89025-46-7,94898-42-7,94898-43-8,101966-50-1,143615-35-4,122741-44-0) → methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside (311778-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 percent / Tf₂O / diethyl ether / 17 h / -25 - 0 °C

2: 83 percent / AcOH; H₂O / 4 h / 60 °C

With trifluoromethylsulfonic anhydride; water; acetic acid; In diethyl ether; 1: Substitution / 2: Hydrolysis;

DOI:10.1080/07328300008544123

upstream raw materials:

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

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride

2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate

methyl 2,3-O-isopropylidene-α-L-rhamnoside

Downstream raw materials:

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

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