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

Base Information

• Chemical Name: 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
• CAS No.: 866332-47-0
• Molecular Formula: C₄₅H₅₄F₆N₂O₂₃S
• Molecular Weight: 1136.98
• Mol file: 866332-47-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 93.0%

C43H52F6N2O22S (866332-39-0) + acetic anhydride (108-24-7) → 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 (866332-47-0)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1016/j.tet.2009.04.022

Reference yield:

methyl (4-methylphenyl 3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (862851-24-9) → 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 (866332-47-0)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 16 h / 20 °C

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

3: 1H-tetrazole / acetonitrile / 0.25 h / 20 °C

4: 77 percent / 3 Angstroem molecular sieves; TMSOTf / acetonitrile / -40 °C

With pyridine; 1H-tetrazole; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; water; In acetone; acetonitrile;

DOI:10.1021/ol0515210

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-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 (866332-47-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / Et₃N / methanol / 1.5 h

2: pyridine / 16 h / 20 °C

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

4: 1H-tetrazole / acetonitrile / 0.25 h / 20 °C

5: 77 percent / 3 Angstroem molecular sieves; TMSOTf / acetonitrile / -40 °C

With pyridine; 1H-tetrazole; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; water; triethylamine; In methanol; 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

(2S,4S,5R,6R)-4-Acetoxy-6-((1R,2R)-1-acetoxy-2,3-dihydroxy-propyl)-2-p-tolylsulfanyl-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl (4-methylphenyl 3,5-dideoxy-8,9-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

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

Downstream raw materials:

C₅₂H₆₁F₆N₂O₂₆P