methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

Base Information

• Chemical Name: methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside
• CAS No.: 278796-53-5
• Molecular Formula: C₇₀H₇₂O₂₀
• Molecular Weight: 1233.33
• Mol file: 278796-53-5.mol

Synonyms:methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

Chemical Property of methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

There total 6 articles about methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-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: 91.0%

methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-2-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside (278796-52-4) → methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside (278796-53-5)

Guidance literature:

With hydrazine hydrate; acetic acid; In methanol; dichloromethane; at 40 ℃; for 3h;

DOI:10.1021/ol005907g

Reference yield:

methyl 5-O-(2-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside (204918-65-0) → methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside (278796-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / N-iodosuccinimide; molecular sieves; silver triflate / CH₂Cl₂ / 2 h / 0 °C

2: 91 percent / AcOH; hydrazine monohydrate / CH₂Cl₂; methanol / 3 h / 40 °C

With N-iodo-succinimide; molecular sieve; silver trifluoromethanesulfonate; hydrazine hydrate; acetic acid; In methanol; dichloromethane;

DOI:10.1021/jo010910e

Reference yield:

ethyl 3,5-di-O-benzyl-2-O-chloroacetyl-1-thio-α-D-arabinofuranoside (278796-48-8) → methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside (278796-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / N-iodosuccinimide; molecular sieves; silver triflate / CH₂Cl₂ / 2 h / 0 °C

2: 91 percent / AcOH; hydrazine monohydrate / CH₂Cl₂; methanol / 3 h / 40 °C

With N-iodo-succinimide; molecular sieve; silver trifluoromethanesulfonate; hydrazine hydrate; acetic acid; In methanol; dichloromethane;

DOI:10.1021/jo010910e

upstream raw materials:

methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-2-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

methyl 5-O-(2-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

ethyl 3,5-di-O-benzyl-2-O-chloroacetyl-1-thio-α-D-arabinofuranoside

ethyl 3,5-di-O-benzyl-1-thio-α-D-arabinofuranoside

Downstream raw materials:

methyl 5-O-{3,5-di-O-(2-O-[2,3,5-tri-O-benzyl-β-D-arabinofuranosyl]-3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl}-2,3-di-O-benzoyl-α-D-arabinofuranoside