methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside
• CAS No.: 934592-21-9
• Molecular Formula: C₄₀H₄₉NO₁₈
• Molecular Weight: 831.825
• Mol file: 934592-21-9.mol

Synonyms:methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside

Chemical Property of methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside

There total 11 articles about methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside 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: 83.0%

methyl (1-adamantyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ylopyranosid)onate (956107-32-7) + methyl 2,6-di-O-benzyl-β-D-galactopyranoside (53685-11-3,58341-66-5,86342-20-3,95015-48-8,100662-78-0,51842-27-4) → methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside (934592-21-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; acetonitrile; at -78 ℃; for 1.5h; Molecular sieve; Inert atmosphere;

DOI:10.1002/anie.201303781

Reference yield:

C26H31NO12S (1151942-33-4) + methyl 2,6-di-O-benzyl-β-D-galactopyranoside → methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside + methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside (934592-21-9)

Guidance literature:

C₂₆H₃₁NO₁₂S; methyl 2,6-di-O-benzyl-β-D-galactopyranoside; With N-iodo-succinimide; In dichloromethane; acetonitrile; at -40 - 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; acetonitrile; at -40 ℃; for 1h; Overall yield = 64 %; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2014.02.006

Reference yield:

C26H31NO12S (1246533-58-3) + methyl 2,6-di-O-benzyl-β-D-galactopyranoside → methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside + methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside (934592-21-9)

Guidance literature:

C₂₆H₃₁NO₁₂S; With di(p-tolyl) sulfoxide; In dichloromethane; at -70 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In dichloromethane; at -70 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

methyl 2,6-di-O-benzyl-β-D-galactopyranoside; In dichloromethane; at -70 - -50 ℃; for 4h; Reagent/catalyst; Temperature; Solvent; Overall yield = 86 %; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2014.02.006

upstream raw materials:

methyl (phenyl-5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate

methyl 2,6-di-O-benzyl-β-D-galactopyranoside

methyl (1-adamantyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ylopyranosid)onate

methyl (phenyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate