1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside

Base Information

• Chemical Name: 1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside
• CAS No.: 265312-92-3
• Molecular Formula: C₃₄H₆₄O₈SSi₃
• Molecular Weight: 717.2

Synonyms:1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside

Chemical Property of 1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside

Chemical Property:

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Technology Process of 1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside

There total 9 articles about 1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-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: 91.6%

t-butyldimethylsiyl triflate (69739-34-0) + 1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose (267900-42-5) → 1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside (265312-92-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1016/S0968-0896(00)00252-2

Reference yield:

2,6-dimethylpyridine (108-48-5) + t-butyldimethylsiyl triflate (69739-34-0) + 1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose (267900-42-5) → 1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside (265312-92-3)

Guidance literature:

In dichloromethane;

Reference yield:

1-O-allyl-α-D-glucopyranoside (7464-56-4,821794-45-0) → 1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside (265312-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83.8 percent / pyridine; DMAP

2: 91.6 percent / 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; In dichloromethane; 1: tosylation / 2: silylation;

DOI:10.1016/S0968-0896(00)00252-2

upstream raw materials:

t-butyldimethylsiyl triflate

1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose

p-toluenesulfonyl chloride

1-O-allyl-α-D-glucopyranoside

Downstream raw materials:

C₅₄H₉₉IO₁₀SSi₃

C₅₂H₉₆IO₁₂SSi₃^(1-)*Na⁽¹⁺⁾

C₃₄H₅₄IO₁₂S^(1-)*Na⁽¹⁺⁾

C₅₄H₉₇I₃O₁₀SSi₃

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