phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside

Base Information

• Chemical Name: phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside
• CAS No.: 1359988-00-3
• Molecular Formula: C₆₃H₅₄O₁₈S
• Molecular Weight: 1131.18

Synonyms:phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside

Chemical Property of phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside

Chemical Property:

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Technology Process of phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside

There total 9 articles about phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside 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: 76.0%

phenyl 2-O-benzoyl-1-thio-α-L-arabinofuranoside (1384897-57-7) + 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate (1359987-79-3) → phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside (1359988-00-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -45 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

DOI:10.1021/jo300084g

Reference yield:

phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside (1359987-96-4) → phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside (1359988-00-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 15 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

3.1: N-Bromosuccinimide / water; ethyl acetate / 4 h / 20 °C

3.2: 2 h / 0 - 20 °C / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -45 °C / Inert atmosphere; Molecular sieve

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo300084g

Reference yield:

phenyl 2,5-di-O-benzoyl-1-thio-α-L-arabinofuranoside (1359987-97-5) → phenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2-O-benzoyl-1-thio-α-L-arabinofuranoside (1359988-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

2.1: N-Bromosuccinimide / water; ethyl acetate / 4 h / 20 °C

2.2: 2 h / 0 - 20 °C / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -45 °C / Inert atmosphere; Molecular sieve

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; water; ethyl acetate;

DOI:10.1021/jo300084g

upstream raw materials:

phenyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-L-arabinofuranoside

phenyl 2-O-benzoyl-3,5-O-(di-tert-butylsilylene)-1-thio-α-L-arabinofuranoside

phenyl 2-O-benzoyl-1-thio-α-L-arabinofuranoside

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate

Downstream raw materials:

C₇₇H₆₈O₂₅

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