methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate

Base Information

• Chemical Name: methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate
• CAS No.: 224035-65-8
• Molecular Formula: C₂₆H₃₀F₃NO₁₂S
• Molecular Weight: 637.585
• Mol file: 224035-65-8.mol

Synonyms:methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate

Chemical Property of methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate

There total 1 articles about methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-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:

Acetoxyacetyl chloride (13831-31-7) + (4S,5R,6R)-4-Acetoxy-5-amino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester; compound with trifluoro-acetic acid → methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate (299179-54-7) + methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate (224035-65-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1016/S0008-6215(02)00003-4

Reference yield: 61.0%

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-galactopyranoside (189744-10-3) + methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate (224035-65-8) → 4-acetoxy-2-[7-hydroxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester (224035-66-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; acetonitrile; at -30 ℃;

DOI:10.1002/(SICI)1521-3773(19990419)38:8<1131::AID-ANIE1131>3.0.CO;2-B

Reference yield:

methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate (224035-65-8) → (2S,4S,5R,6R)-4-Acetoxy-2-((2R,3S,4S,5R)-3-acetoxy-2-acetoxymethyl-5-benzoyloxy-6-hydroxy-tetrahydro-pyran-4-yloxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂; acetonitrile / -30 °C

2: 95 percent / DMAP; pyridine

3: H₂ / Pd-C / acetic acid

4: pyridine

5: 97 percent / CF₃CO₂H / CH₂Cl₂

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; acetic acid; acetonitrile; 1: Substitution / 2: Acylation / 3: Hydrogenolysis / 4: Acetylation / 5: Desilylation;

DOI:10.1002/(SICI)1521-3773(19990419)38:8<1131::AID-ANIE1131>3.0.CO;2-B

upstream raw materials:

Acetoxyacetyl chloride

Downstream raw materials:

4-acetoxy-2-[7-hydroxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

4-acetoxy-2-[3-benzoyloxy-5-hydroxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2→3)-4,6-di-O-acetyl-2-O-benzoyl-β-D-galacotopyranoside

4-acetoxy-2-[7-benzoyloxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester