Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside

Base Information

• Chemical Name: Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside
• CAS No.: 139760-16-0
• Molecular Formula: C₂₆H₃₈O₁₄
• Molecular Weight: 574.579
• Mol file: 139760-16-0.mol

Synonyms:Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside

Chemical Property of Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside

There total 8 articles about Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside 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:

Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside (139760-15-9) → Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside (139760-16-0)

Guidance literature:

With sodium methylate; In toluene; at 50 ℃; for 16h; Yield given;

DOI:10.1021/jo00034a047

Reference yield:

methyl L-rhamnopyranoside (1128-40-1,1198-82-9,2592-55-4,5155-43-1,6340-52-9,10503-91-0,14009-07-5,14687-15-1,14917-55-6,15814-59-2,24332-98-7,34299-65-5,42214-00-6,42214-11-9,57783-34-3,57783-36-5,57783-38-7,57783-40-1,57783-42-3,58525-46-5,58525-47-6,58525-48-7,62182-01-8,62182-02-9,65310-00-1,65941-62-0,68069-80-7,71116-57-9,72274-54-5,72274-55-6,73036-22-3,83198-64-5,85505-15-3,102517-74-8,109718-80-1,109718-81-2,125280-09-3,129172-95-8,63864-94-8) → Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside (139760-16-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1. dibutyltin oxide / 1. toluene, 2 h, reflux; 2. DMF, r.t., 18 h

2: 95 percent / pyridine / 3 h / Ambient temperature

3: 96 percent / H₂ / 5percent palladium-on-charcoal catalyst / ethanol / 3 h

4: 95.8 percent / 2,4,6-trimethylpyridine, silver trifluoromethanesulfonate (AgOTf) / CH₂Cl₂ / 0.25 h

5: 73.5 percent / ZnCl₂, dichloromethyl methyl ether / CHCl₃ / 3 h / Heating

6: 79.8 percent / 2,4,6-trimethylpyridine, silver trifluoromethanesulfonate (AgOTf) / CH₂Cl₂ / 0.08 h

7: 1M methanolic sodium methoxide / toluene / 16 h / 50 °C

With pyridine; 2,4,6-trimethyl-pyridine; Dichloromethyl methyl ether; hydrogen; sodium methylate; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; zinc(II) chloride; palladium on activated charcoal; In ethanol; dichloromethane; chloroform; toluene;

DOI:10.1021/jo00034a047

Reference yield:

Methyl 3-O-benzyl-α-L-rhamnopyranoside (75336-82-2) → Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-α-D-galactopyranoside (139760-16-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / pyridine / 3 h / Ambient temperature

2: 96 percent / H₂ / 5percent palladium-on-charcoal catalyst / ethanol / 3 h

3: 95.8 percent / 2,4,6-trimethylpyridine, silver trifluoromethanesulfonate (AgOTf) / CH₂Cl₂ / 0.25 h

4: 73.5 percent / ZnCl₂, dichloromethyl methyl ether / CHCl₃ / 3 h / Heating

5: 79.8 percent / 2,4,6-trimethylpyridine, silver trifluoromethanesulfonate (AgOTf) / CH₂Cl₂ / 0.08 h

6: 1M methanolic sodium methoxide / toluene / 16 h / 50 °C

With pyridine; 2,4,6-trimethyl-pyridine; Dichloromethyl methyl ether; hydrogen; sodium methylate; silver trifluoromethanesulfonate; zinc(II) chloride; palladium on activated charcoal; In ethanol; dichloromethane; chloroform; toluene;

DOI:10.1021/jo00034a047

upstream raw materials:

Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside

methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside

methyl L-rhamnopyranoside

Methyl 3-O-benzyl-α-L-rhamnopyranoside