methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)-β-D-ribofuranoside

Base Information

• Chemical Name: methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)-β-D-ribofuranoside
• CAS No.: 101024-35-5
• Molecular Formula: C₅₆H₅₈O₂₄
• Molecular Weight: 1115.06
• Mol file: 101024-35-5.mol

Synonyms:

Chemical Property of methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)-β-D-ribofuranoside

Chemical Property:

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)-β-D-ribofuranoside

There total 12 articles about methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)-β-D-ribofuranoside 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%

methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-ribofuranoside (101024-32-2) + 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide (22860-91-9) → methyl 5-O-benzoyl-3-O-(4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylono-1',2-lactone)-β-D-ribofuranoside (101024-34-4) + methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranoside (101024-35-5,101142-00-1) + methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)-β-D-ribofuranoside (101024-35-5,101142-00-1)

Guidance literature:

With silver trifluoromethanesulfonate; Yields of byproduct given;

DOI:10.1016/S0008-6215(00)90455-5

Reference yield: 76.0%

methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-ribofuranoside (101024-32-2) + 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide (22860-91-9) → methyl 5-O-benzoyl-3-O-(4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylono-1',2-lactone)-β-D-ribofuranoside (101024-34-4) + methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranoside (101024-35-5,101142-00-1) + methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)-β-D-ribofuranoside (101024-35-5,101142-00-1)

Guidance literature:

With silver trifluoromethanesulfonate; Yields of byproduct given;

DOI:10.1016/S0008-6215(00)90455-5

Reference yield:

methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl bromide)onate (85382-87-2) → methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranoside (101024-35-5,101142-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 42.5 percent / Hg(CN)2, molecular sieve 4A / acetonitrile / 20 h / Ambient temperature

2: 100 percent / H₂ / PdO / methanol; ethyl acetate / 48 h / Ambient temperature

3: silver triflate

With 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; mercury(II) cyanide; trimethyleneglycol; In methanol; ethyl acetate; acetonitrile;

DOI:10.1016/S0008-6215(00)90455-5

upstream raw materials:

methyl 5-O-benzoyl-3-O-(methyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-ribofuranoside

2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide

methyl 3'-O-benzoyl-β-D-apiofuranoside

methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl bromide)onate