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

Base Information

• Chemical Name: 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate
• CAS No.: 251451-11-3
• Molecular Formula: C₄₇H₃₈Cl₃NO₁₄
• Molecular Weight: 947.176
• Mol file: 251451-11-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate 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:

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate (251451-05-5) → 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate (251451-11-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / Me₃SiOTf / CH₂Cl₂ / 2 h / -42 °C

2: 95 percent / pyridine / 5 h / 20 °C

3: 90 percent AcOH; NaOAc / PdCl₃ / 16 h / 20 °C

4: 1.01 g / K₂CO₃ / 6 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium acetate; potassium carbonate; acetic acid; PdCl₃; In dichloromethane; 1: Etherification / 2: Esterification / 3: Hydrolysis / 4: Etherification;

DOI:10.1016/S0008-6215(00)00159-2

Reference yield:

allyl-α-L-arabinofuranoside (134149-34-1,773896-71-2) → 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate (251451-11-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / Me₃SiOTf / CH₂Cl₂ / 2 h / -42 °C

2: 95 percent / pyridine / 5 h / 20 °C

3: 90 percent AcOH; NaOAc / PdCl₃ / 16 h / 20 °C

4: 1.01 g / K₂CO₃ / 6 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium acetate; potassium carbonate; acetic acid; PdCl₃; In dichloromethane; 1: Etherification / 2: Esterification / 3: Hydrolysis / 4: Etherification;

DOI:10.1016/S0008-6215(00)00159-2

Reference yield:

allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-α-L-arabinofuranoside (251451-10-2) → 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate (251451-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / pyridine / 5 h / 20 °C

2: 90 percent AcOH; NaOAc / PdCl₃ / 16 h / 20 °C

3: 1.01 g / K₂CO₃ / 6 h / 20 °C

With pyridine; sodium acetate; potassium carbonate; acetic acid; PdCl₃; 1: Esterification / 2: Hydrolysis / 3: Etherification;

DOI:10.1016/S0008-6215(00)00159-2

upstream raw materials:

trichloroacetonitrile

allyl-α-L-arabinofuranoside

2,3,5-tri-O-benzoyl-1-O-methyl-α-L-arabinofuranose

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate

Downstream raw materials:

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

(2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-([2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy]methyl)pyrrolidine

(2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine

C₆₅H₆₂Cl₃NO₂₆