Technology Process of (2S,3S,5S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-hexanoic acid methyl ester
There total 15 articles about (2S,3S,5S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-hexanoic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine;
In
water; tert-butyl alcohol;
at 0 ℃;
for 72h;
DOI:10.1016/S0040-4039(03)00744-5
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 69 percent / NaH / dimethylformamide / 4 h / 23 °C
2: 99 percent / n-Bu4N(1+)*F(1-) / tetrahydrofuran / 2 h / 23 °C
3: 87 percent / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 2 h / 23 °C
4: 71 percent / tetrahydrofuran / 3 h / -78 °C
5: 62 percent / Et3N / CH2Cl2 / 1 h / 0 °C
6: 90 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 14 h / 40 °C
7: NaOH / tetrahydrofuran; H2O / 14 h / 0 °C
8: imidazole / dimethylformamide / 18 h / 23 °C
9: diethyl ether / 0.5 h / 0 °C
10: OsO4; NMO / methanol; H2O / 6 h / 23 °C
With
1H-imidazole; sodium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
3: Dess-Martin oxidation / 4: Brown's allylboration;
DOI:10.1016/S0040-4039(03)00744-5
- Guidance literature:
-
Multi-step reaction with 13 steps
1: AD mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 36 h / 0 °C
2: 92 percent / PPTS / acetone / 5 h / 23 °C
3: 97 percent / LiBH4 / tetrahydrofuran / 2 h / 0 °C
4: 69 percent / NaH / dimethylformamide / 4 h / 23 °C
5: 99 percent / n-Bu4N(1+)*F(1-) / tetrahydrofuran / 2 h / 23 °C
6: 87 percent / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 2 h / 23 °C
7: 71 percent / tetrahydrofuran / 3 h / -78 °C
8: 62 percent / Et3N / CH2Cl2 / 1 h / 0 °C
9: 90 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 14 h / 40 °C
10: NaOH / tetrahydrofuran; H2O / 14 h / 0 °C
11: imidazole / dimethylformamide / 18 h / 23 °C
12: diethyl ether / 0.5 h / 0 °C
13: OsO4; NMO / methanol; H2O / 6 h / 23 °C
With
1H-imidazole; sodium hydroxide; AD-mix-α; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; methanesulfonamide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
1: Sharpless asymmetric dihydroxylation / 6: Dess-Martin oxidation / 7: Brown's allylboration;
DOI:10.1016/S0040-4039(03)00744-5