Technology Process of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4R,5S,6S)-4,5-bis-acetylamino-2-formyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester
There total 12 articles about Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4R,5S,6S)-4,5-bis-acetylamino-2-formyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester which
guide to synthetic route it.
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synthetic route:
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297733-61-0
Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4R,5S,6S)-4,5-bis-acetylamino-2-formyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: 50 percent / pyridine / 70 h / 20 °C
2.1: Bu4NHSO4; NaOH; K2CO3 / toluene; dimethylsulfoxide; butan-1-ol / 2 h / 20 °C
3.1: NaN3; NH4Cl / dimethylsulfoxide / 20 h / 80 °C
4.1: CH2Cl2; pyridine / 2.5 h / 0 - 20 °C
5.1: NaN3 / dimethylsulfoxide / 0.5 h / 20 °C
6.1: 44 percent / 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 70 h / 20 °C
7.1: 73 percent / sodium cyanoborohydride; 3 Angstroem molecular sieves; fluoroboric acid / tetrahydrofuran; diethyl ether / 4 h / 0 °C
8.1: 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 14 h / 20 °C
8.2: H2S; Et3N / pyridine; H2O / 1.92 h
8.3: 40 percent / pyridine / 1.5 h
9.1: H2 / 10 percent Pd-C / ethanol; ethyl acetate / 5 h
10.1: DMSO; Ac2O / 6 h / 20 °C
With
sodium hydroxide; tetrafluoroboric acid; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; acetic anhydride; sodium cyanoborohydride; potassium carbonate; ammonium chloride; dimethyl sulfoxide; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; butan-1-ol;
1.1: Tosylation / 2.1: Substitution / 3.1: Substitution / 4.1: Acylation / 5.1: Substitution / 6.1: glycosylation / 7.1: Reduction / 8.1: glycosylation / 8.2: Reduction / 8.3: Acetylation / 9.1: Catalytic hydrogenation / 10.1: Oxidation;
DOI:10.1016/S0008-6215(99)00318-3
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297733-61-0
Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4R,5S,6S)-4,5-bis-acetylamino-2-formyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester
- Guidance literature:
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Multi-step reaction with 5 steps
1.1: 44 percent / 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 70 h / 20 °C
2.1: 73 percent / sodium cyanoborohydride; 3 Angstroem molecular sieves; fluoroboric acid / tetrahydrofuran; diethyl ether / 4 h / 0 °C
3.1: 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 14 h / 20 °C
3.2: H2S; Et3N / pyridine; H2O / 1.92 h
3.3: 40 percent / pyridine / 1.5 h
4.1: H2 / 10 percent Pd-C / ethanol; ethyl acetate / 5 h
5.1: DMSO; Ac2O / 6 h / 20 °C
With
tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; hydrogen; acetic anhydride; sodium cyanoborohydride; dimethyl sulfoxide; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate;
1.1: glycosylation / 2.1: Reduction / 3.1: glycosylation / 3.2: Reduction / 3.3: Acetylation / 4.1: Catalytic hydrogenation / 5.1: Oxidation;
DOI:10.1016/S0008-6215(99)00318-3
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297733-61-0
Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4R,5S,6S)-4,5-bis-acetylamino-2-formyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: NaN3; NH4Cl / dimethylsulfoxide / 20 h / 80 °C
2.1: CH2Cl2; pyridine / 2.5 h / 0 - 20 °C
3.1: NaN3 / dimethylsulfoxide / 0.5 h / 20 °C
4.1: 44 percent / 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 70 h / 20 °C
5.1: 73 percent / sodium cyanoborohydride; 3 Angstroem molecular sieves; fluoroboric acid / tetrahydrofuran; diethyl ether / 4 h / 0 °C
6.1: 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves; dimethyl(thiomethyl)sulfonium triflate / CH2Cl2 / 14 h / 20 °C
6.2: H2S; Et3N / pyridine; H2O / 1.92 h
6.3: 40 percent / pyridine / 1.5 h
7.1: H2 / 10 percent Pd-C / ethanol; ethyl acetate / 5 h
8.1: DMSO; Ac2O / 6 h / 20 °C
With
tetrafluoroboric acid; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; hydrogen; acetic anhydride; sodium cyanoborohydride; ammonium chloride; dimethyl sulfoxide; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate;
1.1: Substitution / 2.1: Acylation / 3.1: Substitution / 4.1: glycosylation / 5.1: Reduction / 6.1: glycosylation / 6.2: Reduction / 6.3: Acetylation / 7.1: Catalytic hydrogenation / 8.1: Oxidation;
DOI:10.1016/S0008-6215(99)00318-3