phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside
• CAS No.: 146399-77-1
• Molecular Formula: C₂₂H₂₆O₄S
• Molecular Weight: 386.512
• Mol file: 146399-77-1.mol

Synonyms:phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Chemical Property of phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

There total 7 articles about phenyl 4-O-benzyl-2,3-O-isopropylidene-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: 95.0%

benzyl bromide (100-39-0) + phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (153693-37-9) → phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (146399-77-1)

Guidance literature:

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2005.03.007

Reference yield: 83.0%

benzyl bromide (100-39-0) + phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (131087-35-9) → phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (146399-77-1)

Guidance literature:

With sodium hydride; In DMF (N,N-dimethyl-formamide);

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (146399-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.38 g / TsOH / various solvent(s) / 20 h

2: KH / dimethylformamide / 0.25 h / Ambient temperature

With potassium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89043-8

upstream raw materials:

benzyl bromide

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

phenyl 1-thio-α-L-rhamnopyranose

Downstream raw materials:

phenyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside