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

Base Information

• Chemical Name: methyl [phenyl 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(R)-3-²H-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate
• CAS No.: 1606160-21-7
• Molecular Formula: C₂₃H₂₇NO₁₁S
• Molecular Weight: 526.526

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

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

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

There total 4 articles about methyl [phenyl 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(R)-3-²H-3,5-dideoxy-2-thio-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: 42.0%

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 (1606160-01-3) + 4-Nitrophenyl chloroformate (7693-46-1) → methyl [phenyl 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(R)-3-2H-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate (1606160-21-7)

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;

4-Nitrophenyl chloroformate; With sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃; for 8h;

With acetic anhydride; In pyridine; at 20 ℃; for 16h;

DOI:10.1021/ol500917k

Reference yield:

C20H27(2)HClNO12 → methyl [phenyl 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(R)-3-2H-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate (1606160-21-7)

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: 8 h / 0 °C

2.3: 16 h / 20 °C

With methanesulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/ol500917k

Reference yield:

N-acetyl neuraminic acid (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) → methyl [phenyl 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(R)-3-2H-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate (1606160-21-7)

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: 8 h / 0 °C

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

upstream raw materials:

N-acetyl neuraminic acid

C₂₂H₃₀⁽²⁾HNO₁₄

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

4-Nitrophenyl chloroformate

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