p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 943221-82-7
• Molecular Formula: C₂₁H₃₄O₅SSi
• Molecular Weight: 426.649

Synonyms:p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-1-thio-α-L-rhamnopyranoside

Chemical Property of p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

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Technology Process of p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-1-thio-α-L-rhamnopyranoside

There total 2 articles about p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-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: 99.9%

p-tolyl 4-O-acetyl-1-thio-α-L-rhamnopyranoside (943221-81-6) + tert-butyldimethylsilyl chloride (18162-48-6) → p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-1-thio-α-L-rhamnopyranoside (943221-82-7)

Guidance literature:

With 1H-imidazole; In pyridine; at 20 ℃; for 12h;

DOI:10.1016/j.carres.2007.03.014

Reference yield:

p-tolyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (851625-43-9) → p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-1-thio-α-L-rhamnopyranoside (943221-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93.1 percent / AcOH; water / 1.5 h / 80 °C

2: 99.9 percent / imidazole / pyridine / 12 h / 20 °C

With 1H-imidazole; water; acetic acid; In pyridine;

DOI:10.1016/j.carres.2007.03.014

Reference yield: 83.9%

p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-1-thio-α-L-rhamnopyranoside (943221-82-7) + levulinic acid (123-76-2) → p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside (943221-77-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 12h;

DOI:10.1016/j.carres.2007.03.014

upstream raw materials:

p-tolyl 4-O-acetyl-1-thio-α-L-rhamnopyranoside

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

p-tolyl 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside

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