allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside
• CAS No.: 607364-84-1
• Molecular Formula: C₅₅H₅₈O₁₅Si
• Molecular Weight: 987.142

Synonyms:allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Chemical Property of allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

There total 3 articles about allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-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: 78.4%

2,3-5-tri-O-benzoyl-α-D-arabinofuranosyl 2,2,2-trichloroacetimidate + allyl 2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside (607364-83-0) → allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside (607364-84-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1081/CAR-120023470

Reference yield:

Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside (127446-71-3) → allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside (607364-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / imidazole / dimethylformamide / 4 h / 20 °C

2: 78.4 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/CAR-120023470

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside (607364-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / imidazole / dimethylformamide / 4 h / 20 °C

2: 78.4 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/CAR-120023470

upstream raw materials:

allyl 2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside

tert-butyldimethylsilyl chloride

Downstream raw materials:

allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-α-D-glucopyranoside

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