methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• CAS No.: 1447700-91-5
• Molecular Formula: C₄₆H₄₉NO₁₈S
• Molecular Weight: 935.957
• Mol file: 1447700-91-5.mol

Synonyms:methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property of methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-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-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

There total 2 articles about methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-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: 75.0%

Benzoic acid (4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (873298-71-6) + methyl (5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate (1219717-79-9) → methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside + methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1447700-91-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; at -78 ℃; Overall yield = 83 percent;

DOI:10.1021/acs.jmedchem.0c01186

Reference yield:

Benzoic acid (4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (873298-71-6) + methyl (5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate (1219717-81-3) → methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside + methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1447700-91-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; at -50 - 20 ℃; optical yield given as %de; chemoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.200903035

Reference yield: 57.0%

methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->3)-p-tolyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1447700-91-5) + C45H57N5O19 (1219717-85-7) → C84H98N6O37

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - -40 ℃; chemoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.200903035

upstream raw materials:

Benzoic acid (4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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

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