phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside

Base Information

• Chemical Name: phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside
• CAS No.: 1359987-96-4
• Molecular Formula: C₄₁H₄₀O₆SSi
• Molecular Weight: 688.917

Synonyms:phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside

Chemical Property of phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside

There total 3 articles about phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-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: 84.0%

methyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-α-L-arabinofuranoside (1359987-95-3) + thiophenol (108-98-5) → phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside (1359987-96-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/jo300084g

Reference yield:

2,5-O-dibenzoyl-1-methyl-α-L-arabinofuranoside → phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside (1359987-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo300084g

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → phenyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-1-thio-α-L-arabinofuranoside (1359987-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo300084g

upstream raw materials:

methyl 2,5-di-O-benzoyl-3-O-tert-butyldiphenylsilyl-α-L-arabinofuranoside

thiophenol

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

phenyl 2,5-di-O-benzoyl-1-thio-α-L-arabinofuranoside

phenyl 2,3,6-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2,5-di-O-benzoyl-1-thio-α-L-arabinofuranoside

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

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