(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

Base Information

• Chemical Name: (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
• CAS No.: 866332-36-7
• Molecular Formula: C₂₃H₂₈F₃NO₁₀S
• Molecular Weight: 567.537
• Mol file: 866332-36-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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: 78.0%

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) → (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 (866332-36-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1021/ol0515210

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 → (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 (866332-36-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 977 mg / pyridine / 16 h / 20 °C

2: 78 percent / aq. TFA / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; trifluoroacetic acid; In dichloromethane;

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) → (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 (866332-36-7)

Guidance literature:

Multi-step reaction with 3 steps

1: p-TSA / acetone / 0.5 h / 20 °C

2: 977 mg / pyridine / 16 h / 20 °C

3: 78 percent / aq. TFA / CH₂Cl₂ / 0.17 h / 0 °C

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

DOI:10.1021/ol0515210

upstream raw materials:

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

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

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