Technology Process of (2S,5S)-2-tert-Butyl-5-(hydroxy-{(2S,6R,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methyl)-5-methyl-[1,3]dioxolan-4-one
There total 20 articles about (2S,5S)-2-tert-Butyl-5-(hydroxy-{(2S,6R,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methyl)-5-methyl-[1,3]dioxolan-4-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 78 percent / H2 / Pd/C / ethyl acetate / 6 h / 760.05 Torr
2.1: 75 percent / PCC; 4 Angstroem molecular sieves / CH2Cl2 / 22 h / 20 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C
3.2: 87 percent / tetrahydrofuran; hexane / 0.83 h / -78 °C
4.1: 97 percent / Et3N; 4-N,N-(dimethylamino)pyridine / CH2Cl2 / 0.58 h / 0 °C
5.1: CuI / tetrahydrofuran; diethyl ether / -78 - -40 °C
5.2: 99 percent / tetrahydrofuran; diethyl ether / 0.42 h / -78 °C
6.1: 76 percent / TsOH*H2O / benzene / 2.5 h / 20 °C
7.1: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C
8.1: 90 percent / 4 Angstroem molecular sieves; tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide / CH2Cl2 / 0.5 h / 20 °C
9.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C
9.2: tetrahydrofuran; hexane / 0.33 h / -78 °C
With
dmap; copper(l) iodide; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; benzene;
DOI:10.1021/jo001433n
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 97 percent / Et3N; 4-N,N-(dimethylamino)pyridine / CH2Cl2 / 0.58 h / 0 °C
2.1: CuI / tetrahydrofuran; diethyl ether / -78 - -40 °C
2.2: 99 percent / tetrahydrofuran; diethyl ether / 0.42 h / -78 °C
3.1: 76 percent / TsOH*H2O / benzene / 2.5 h / 20 °C
4.1: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C
5.1: 90 percent / 4 Angstroem molecular sieves; tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide / CH2Cl2 / 0.5 h / 20 °C
6.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C
6.2: tetrahydrofuran; hexane / 0.33 h / -78 °C
With
dmap; copper(l) iodide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/jo001433n
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: CuI / tetrahydrofuran; diethyl ether / -78 - -40 °C
1.2: 99 percent / tetrahydrofuran; diethyl ether / 0.42 h / -78 °C
2.1: 76 percent / TsOH*H2O / benzene / 2.5 h / 20 °C
3.1: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C
4.1: 90 percent / 4 Angstroem molecular sieves; tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide / CH2Cl2 / 0.5 h / 20 °C
5.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C
5.2: tetrahydrofuran; hexane / 0.33 h / -78 °C
With
copper(l) iodide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/jo001433n
