methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate

Base Information

• Chemical Name: methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate
• CAS No.: 866332-57-2
• Molecular Formula: C₂₇H₃₂F₃NO₁₂S
• Molecular Weight: 651.612
• Mol file: 866332-57-2.mol

Synonyms:methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate

Chemical Property of methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate

There total 2 articles about methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate 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: 98.0%

methyl (4-methylphenyl 3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (862851-24-9) + acetic anhydride (108-24-7) → methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate (866332-57-2)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1016/j.tet.2009.04.022

Reference yield:

(2S,4S,5R,6R)-5-Amino-4-hydroxy-2-p-tolylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (374573-40-7) → methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate (866332-57-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Et₃N / methanol / 1.5 h

2: pyridine / 16 h / 20 °C

With pyridine; triethylamine; In methanol;

DOI:10.1021/ol0515210

Reference yield:

methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate (866332-57-2) → dibenzyl [methyl (4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid)ulonate] phosphite (866332-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N-bromosuccinimide; H₂O / acetone / 0.5 h / 20 °C

2: 1H-tetrazole / acetonitrile / 0.25 h / 20 °C

With 1H-tetrazole; N-Bromosuccinimide; water; In acetone; acetonitrile;

DOI:10.1021/ol0515210

upstream raw materials:

methyl (4-methylphenyl 3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

acetic anhydride

(2S,4S,5R,6R)-5-Amino-4-hydroxy-2-p-tolylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

dibenzyl [methyl (4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid)ulonate] phosphite

C₄₃H₅₂F₆N₂O₂₂S

methyl 4,7,8-tri-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-9-O-(methyl-5-trifluoroacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosidonate

C₅₂H₆₁F₆N₂O₂₆P