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

Base Information

• Chemical Name: allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-L-arabinofuranoside
• CAS No.: 313468-67-6
• Molecular Formula: C₄₈H₄₆O₁₂
• Molecular Weight: 814.886

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

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

Chemical Property:

Purity/Quality:

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

There total 5 articles about allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-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: 73.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-α-L-arabinofuranoside (251451-10-2) → allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-L-arabinofuranoside (313468-67-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -10 ℃; for 4h;

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

Reference yield:

allyl-α-L-arabinofuranoside (134149-34-1,773896-71-2) → allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-L-arabinofuranoside (313468-67-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 73 percent / Me₃SiOTf / CH₂Cl₂ / 4 h / -10 °C

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1: Etherification / 2: Etherification;

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

Reference yield:

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate (251451-05-5) → allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-L-arabinofuranoside (313468-67-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 73 percent / Me₃SiOTf / CH₂Cl₂ / 4 h / -10 °C

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1: Etherification / 2: Etherification;

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

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

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

allyl-α-L-arabinofuranoside

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

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-arabinofuranoside

C₆₅H₆₂Cl₃NO₂₆

C₆₆H₆₆O₂₆

(2R,3R,4R,5S)-2-((2S,3S,4R,5R)-5-Allyloxy-3,4-bis-benzyloxy-tetrahydro-furan-2-ylmethoxy)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

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