methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside

Base Information

• Chemical Name: methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside
• CAS No.: 868381-74-2
• Molecular Formula: C₄₄H₅₂O₁₁S
• Molecular Weight: 788.956
• Mol file: 868381-74-2.mol

Synonyms:methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside

Chemical Property of methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside

There total 3 articles about methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-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: 59.0%

3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-D-rhamnopyranosyl N-phenyltrifluoroacetimidate (868381-69-5) + methyl 2,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside (112612-46-1) → methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-βaD-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside (868381-72-0) + methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside (868381-74-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -60 - -25 ℃; for 4h;

DOI:10.1021/jo051153d

Reference yield:

Phenyl-methanesulfonic acid (3S,4S,5R,6R)-4-allyloxy-5-benzyloxy-2-(diphenoxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester (868381-67-3) + methyl 2,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside (112612-46-1) → methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-βaD-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside (868381-72-0) + methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside (868381-74-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - -15 ℃;

DOI:10.1021/jo051153d

Reference yield:

3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-D-rhamnopyranose → methyl (3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside (868381-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / NaH / CH₂Cl₂ / 4 h / 0 °C

2: 59 percent / TMSOTf / CH₂Cl₂ / 4 h / -60 - -25 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; In dichloromethane;

DOI:10.1021/jo051153d

upstream raw materials:

3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-D-rhamnopyranosyl N-phenyltrifluoroacetimidate

methyl 2,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside

Phenyl-methanesulfonic acid (3S,4S,5R,6R)-4-allyloxy-5-benzyloxy-2-(diphenoxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Downstream raw materials:

4-methoxyphenyl 3-O-allyl-2-O-benzylsulfonyl-4-O-benzyl-β-D-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside

methyl (3,3-diacetamido-4-O-acetyl-2-O-benzyl-α-D-fucopyranosyl)-(1->2)-(3-O-allyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside

methyl (3-O-allyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside