methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Base Information

Chemical Name:methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
CAS No.:1453411-82-9
Molecular Formula:C₂₆H₃₅N₃O₁₃
Molecular Weight:597.576
Hs Code.:

Synonyms:methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

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Chemical Property of methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

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Technology Process of methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

There total 6 articles about methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-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: 68.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 1453411-79-4
methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

: 1453411-82-9
methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Guidance literature:: formaldehyd; methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate; In methanol; at 20 ℃; for 2h;

With sodium cyanoborohydride;
DOI:10.1021/ja405916q

Reference yield:

: 108740-39-2,6931-68-6,72690-21-2,73208-82-9,108740-37-0,108740-38-1,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,74006-95-4
(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

: 1453411-82-9
methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Guidance literature:: Multi-step reaction with 6 steps

1.1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 50 °C / Inert atmosphere

2.1: trimethylsilylazide / tert-butyl alcohol / 12 h / 80 °C / Inert atmosphere

3.1: lithium chloride / 2 h / 0.2 Torr / Molecular sieve

4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 0 - 20 °C

5.1: triphenylphosphine / tetrahydrofuran / 12 h / 20 °C

5.2: 24 h / 20 °C

6.1: methanol / 2 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; methanol; ethyl acetate; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja405916q

Reference yield:

: 163860-77-3
methyl (5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate chloride

: 1453411-82-9
methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 0 - 20 °C

2.1: triphenylphosphine / tetrahydrofuran / 12 h / 20 °C

2.2: 24 h / 20 °C

3.1: methanol / 2 h / 20 °C

With N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1021/ja405916q