methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 115678-25-6
• Molecular Formula: C₅₅H₆₆O₁₈
• Molecular Weight: 1015.12
• Mol file: 115678-25-6.mol

Synonyms:methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property of methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside

There total 9 articles about methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-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: 34.0%

methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside (69558-07-2) + methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (115678-24-5) → methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside (115678-25-6)

Guidance literature:

With 4 A molecular sieve; nitrosonium tetrafluoroborate; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/jo00252a030

Reference yield:

2,3,4,6-tetra-O-acetyl-α-L mannopyranosyl bromide (61303-35-3) → methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside (115678-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / 4-A molecular sieves, N,N,N'N'-tetramethylurea, silver trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / -40 - 25 °C

2: 34 percent / 4-A molecular sieves, nitrosyl tetrafluoroborate / CH₂Cl₂ / 2 h / 25 °C

With 4 A molecular sieve; silver trifluoromethanesulfonate; nitrosonium tetrafluoroborate; tetramethylurea; In dichloromethane;

DOI:10.1021/jo00252a030

Reference yield:

benzyl bromide (100-39-0) → methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside (115678-25-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) DMF, 1 h, 2.) 10 deg C, 2 h

2: 86.4 percent / trifluoroacetic acid / methanol / 2 h / 50 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylamonium bromide / 1.) C₆H₆, reflux, 5 h, 2.) 50 deg C, 3 h

4: 42 percent / 4-A molecular sieves, N,N,N'N'-tetramethylurea, silver trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / -40 - 25 °C

5: 34 percent / 4-A molecular sieves, nitrosyl tetrafluoroborate / CH₂Cl₂ / 2 h / 25 °C

With 4 A molecular sieve; tetrabutylammomium bromide; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; nitrosonium tetrafluoroborate; trifluoroacetic acid; tetramethylurea; In methanol; dichloromethane;

DOI:10.1021/jo00252a030

upstream raw materials:

methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside

methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

2,3,4,6-tetra-O-acetyl-α-L mannopyranosyl bromide

benzyl bromide