ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside
• CAS No.: 883556-88-5
• Molecular Formula: C₂₁H₃₄O₅SSi
• Molecular Weight: 426.649

Synonyms:ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

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Technology Process of ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

There total 1 articles about ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside 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: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8) → ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside (883556-88-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield: 98.0%

ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside (883556-88-5) + benzoyl chloride (98-88-4) → ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside (460741-88-2)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 80 ℃;

Reference yield: 82.0%

ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside (883556-88-5) + levulinic acid (123-76-2) → ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-levulinoyl-1-thio-β-D-glucopyranoside (946076-02-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.3762/bjoc.13.19

upstream raw materials:

tert-butyldimethylsilyl chloride

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-levulinoyl-1-thio-β-D-glucopyranoside

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