phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 709619-81-8
• Molecular Formula: C₁₉H₂₈O₆S
• Molecular Weight: 384.494
• Mol file: 709619-81-8.mol

Synonyms:phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside

Chemical Property of phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside

There total 3 articles about phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-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: 88.0%

phenyl (2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside (202824-32-6) + methyl iodide (74-88-4) → phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside (709619-81-8)

Guidance literature:

phenyl (2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.333333h;

methyl iodide; at 0 - 20 ℃; for 2.5h;

DOI:10.1002/anie.201403542

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside (709619-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / camphor sulfonic acid / methanol / 72 h / Heating

2: 67 percent / NaH / tetrahydrofuran / 2 h / 20 °C

With camphor-10-sulfonic acid; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1016/j.tet.2004.03.021

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) + 2,2,3,3-tetramethoxybutane (176798-33-7) → phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside (709619-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (1S)-10-camphorsulfonic acid; trimethyl orthoformate / methanol / Inert atmosphere; Reflux

2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 0 °C

2.2: 2.5 h / 0 - 20 °C

With (1S)-10-camphorsulfonic acid; sodium hydride; trimethyl orthoformate; In methanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/anie.201403542

upstream raw materials:

phenyl (2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside

methyl iodide

phenyl 1-thio-α-L-rhamnopyranose

2,2,3,3-tetramethoxybutane

Downstream raw materials:

C₁₃H₁₈O₄S

C₂₅H₄₆O₄SSi₂

C₂₅H₄₆O₅SSi₂