methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Base Information

• Chemical Name: methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate
• CAS No.: 261164-47-0
• Molecular Formula: C₂₄H₂₉N₅O₉S
• Molecular Weight: 563.588
• Mol file: 261164-47-0.mol

Synonyms:methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Chemical Property of methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

There total 7 articles about methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)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: 95.0%

acetic anhydride (108-24-7) + methyl (phenyl 5-acetamido-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (328898-10-8) → methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (261164-47-0)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1016/S0008-6215(00)00267-6

Reference yield:

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate (118977-25-6) → methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (261164-47-0)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOMe / methanol / 2 h / 0 °C

2: Amberlite IRA₁₂₀ (H⁺) resin / 13 h / 20 °C

3: molecular sieves 4 Angstroem; Ag₂O; n-Bu₄NI / CH₂Cl₂ / 48 h

4: 80 percent AcOH / 0.5 h / 80 - 90 °C

5: 64 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

6: 74 percent / NaN₃; 18-crown-6 / dimethylformamide / 20 h / 60 °C

7: 95 percent / pyridine / 0 - 20 °C

With pyridine; sodium azide; 18-crown-6 ether; 4 A molecular sieve; Amberlite IRA₁₂₀ (H⁺) resin; sodium methylate; tetra-(n-butyl)ammonium iodide; acetic acid; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)00267-6

Reference yield:

methyl (phenyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-β-D-galactonon-2-ulopyranoside)onate (221909-84-8) → methyl (phenyl 5-acetamido-7,8-di-O-acetyl-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (261164-47-0)

Guidance literature:

Multi-step reaction with 6 steps

1: Amberlite IRA₁₂₀ (H⁺) resin / 13 h / 20 °C

2: molecular sieves 4 Angstroem; Ag₂O; n-Bu₄NI / CH₂Cl₂ / 48 h

3: 80 percent AcOH / 0.5 h / 80 - 90 °C

4: 64 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

5: 74 percent / NaN₃; 18-crown-6 / dimethylformamide / 20 h / 60 °C

6: 95 percent / pyridine / 0 - 20 °C

With pyridine; sodium azide; 18-crown-6 ether; 4 A molecular sieve; Amberlite IRA₁₂₀ (H⁺) resin; tetra-(n-butyl)ammonium iodide; acetic acid; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)00267-6

upstream raw materials:

acetic anhydride

methyl (phenyl 5-acetamido-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate

methyl (phenyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-β-D-galactonon-2-ulopyranoside)onate