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

Base Information

• Chemical Name: methyl (4-methylphenyl 3,5-dideoxy-8,9-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
• CAS No.: 866332-40-3
• Molecular Formula: C₂₆H₃₂F₃NO₁₀S
• Molecular Weight: 607.602
• Mol file: 866332-40-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(2S,4S,5R,6R)-6-[(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-2-p-tolylsulfanyl-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester + acetic anhydride (108-24-7) → methyl (4-methylphenyl 3,5-dideoxy-8,9-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (866332-40-3)

Guidance literature:

With pyridine; at 20 ℃; for 16h;

DOI:10.1021/ol0515210

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-methylphenyl 3,5-dideoxy-8,9-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (866332-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TSA / acetone / 0.5 h / 20 °C

2: 977 mg / pyridine / 16 h / 20 °C

With pyridine; toluene-4-sulfonic acid; In acetone;

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-methylphenyl 3,5-dideoxy-8,9-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate (866332-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / Et₃N / methanol / 1.5 h

2: p-TSA / acetone / 0.5 h / 20 °C

3: 977 mg / pyridine / 16 h / 20 °C

With pyridine; toluene-4-sulfonic acid; triethylamine; In methanol; acetone;

DOI:10.1021/ol0515210

upstream raw materials:

acetic anhydride

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

(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:

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

(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