methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate

Base Information

Chemical Name:methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate
CAS No.:1606160-15-9
Molecular Formula:C₂₆H₃₀F₃NO₁₂S
Molecular Weight:638.577
Hs Code.:

Synonyms:methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate

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Chemical Property of methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate

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Technology Process of methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate

There total 5 articles about methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]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: 73.0%

: 431-47-0
trifluoroacetic acid-methyl ester

: 1606160-01-3
methyl [phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3(R)-3-²H-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate

: 1606160-15-9
methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate

Guidance literature:: methyl [phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3(R)-3-²H-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate; With methanesulfonic acid; In methanol; at 60 ℃; for 72h;

trifluoroacetic acid-methyl ester; With triethylamine; In methanol; at 20 ℃; for 1h; Inert atmosphere;

With acetic anhydride; In pyridine; at 20 ℃; for 16h;
DOI:10.1021/ol500917k

Reference yield:

: C₂₀H₂₇⁽²⁾HClNO₁₂

: 1606160-15-9
methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C

2.1: methanesulfonic acid / methanol / 72 h / 60 °C

2.2: 1 h / 20 °C / Inert atmosphere

2.3: 16 h / 20 °C

With methanesulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
DOI:10.1021/ol500917k

Reference yield:

: 6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9
N-acetyl neuraminic acid

: 1606160-15-9
methyl [phenyl 4,7,8,9-tetra-O-acetyl-3-(R)-3-2H-3,5-dideoxy-2-thio-5-trifluroacetamido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate

Guidance literature:: Multi-step reaction with 6 steps

1.1: [D]-sodium hydroxide / water-d2 / 0.5 h / pH 8

2.1: Dowex 650C (H⁺) cationic exchange resin / 16 h

3.1: pyridine / 16 h

4.1: acetyl chloride / methanol / 16 h / 0 - 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C

6.1: methanesulfonic acid / methanol / 72 h / 60 °C

6.2: 1 h / 20 °C / Inert atmosphere

6.3: 16 h / 20 °C

With methanesulfonic acid; [D]-sodium hydroxide; N-ethyl-N,N-diisopropylamine; acetyl chloride; In pyridine; methanol; dichloromethane; water-d2;
DOI:10.1021/ol500917k