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

Base Information

• Chemical Name: Phenyl-methanesulfonic acid (3S,4S,5R,6R)-4-allyloxy-5-benzyloxy-2-(diphenoxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 868381-67-3
• Molecular Formula: C₃₅H₃₇O₁₀PS
• Molecular Weight: 680.713
• Mol file: 868381-67-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Phenyl-methanesulfonic acid (3S,4S,5R,6R)-4-allyloxy-5-benzyloxy-2-(diphenoxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester 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:

3-O-allyl-2-O-benzenesulfonyl-4-O-benzyl-D-rhamnopyranose + chlorophosphoric acid diphenyl ester (2524-64-3) → Phenyl-methanesulfonic acid (3S,4S,5R,6R)-4-allyloxy-5-benzyloxy-2-(diphenoxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester (868381-67-3)

Guidance literature:

With dmap; In dichloromethane; at -10 ℃;

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:

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 (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 (868381-91-3)

Guidance literature:

Multi-step reaction with 3 steps

1: TMSOTf / CH₂Cl₂ / -78 - -15 °C

2: 62 percent / NaNH₂ / dimethylformamide / 96 h / 20 °C

3: 40 percent / TfOH; NIS / CH₂Cl₂; diethyl ether / 1.5 h / -20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; sodium amide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo051153d

upstream raw materials:

chlorophosphoric acid diphenyl ester

Downstream raw materials:

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

methyl (3-O-allyl-2-O-benzenesulfonyl-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

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