methyl (phenyl 5-acetamido-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-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate
CAS No.:328898-10-8
Molecular Formula:C₂₀H₂₅N₅O₇S
Molecular Weight:479.514
Hs Code.:

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

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

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

There total 6 articles about methyl (phenyl 5-acetamido-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: 74.0%

: 328898-09-5
methyl (phenyl 5-acetamido-4-O-cyanomethyl-3,5-dideoxy-9-p-tolylsulfonyl-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

: 328898-10-8
methyl (phenyl 5-acetamido-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Guidance literature:: With sodium azide; 18-crown-6 ether; In N,N-dimethyl-formamide; at 60 ℃; for 20h;
DOI:10.1016/S0008-6215(00)00267-6

Reference yield:

: 118977-25-6
methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate

: 328898-10-8
methyl (phenyl 5-acetamido-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 6 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

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:

: 221909-84-8
methyl (phenyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-β-D-galactonon-2-ulopyranoside)onate

: 328898-10-8
methyl (phenyl 5-acetamido-9-azido-4-O-cyanomethyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 5 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

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