Technology Process of (2R,4R,5R,7S,9S,10S,12R,1'R/S,4'S/R,5'S/R,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-(4,5-epoxy-1-hydroxy-4-methylhexan-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene
There total 12 articles about (2R,4R,5R,7S,9S,10S,12R,1'R/S,4'S/R,5'S/R,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-(4,5-epoxy-1-hydroxy-4-methylhexan-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene which
guide to synthetic route it.
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synthetic route:
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223565-08-0
(E)-(2R,4R,5R,7S,9S,10S,12R,1'S,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-ethyl-2-(1-hydroxy-4-methylhex-4-en-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene
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337533-69-4
(2R,4R,5R,7S,9S,10S,12R,1'R/S,4'S/R,5'S/R,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-(4,5-epoxy-1-hydroxy-4-methylhexan-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene
- Guidance literature:
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With
3,3-dimethyldioxirane; potassium carbonate;
In
acetone;
at 0 ℃;
for 1h;
DOI:10.1039/b008159k
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337533-69-4
(2R,4R,5R,7S,9S,10S,12R,1'R/S,4'S/R,5'S/R,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-(4,5-epoxy-1-hydroxy-4-methylhexan-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C
2.1: Amberlite resin IR 118
3.1: 90 mg / Et3N; 4-DMAP / CH2Cl2 / 1 h / 20 °C
4.1: H2; K2CO3 / Lindlar catalyst / pentane; ethyl acetate / 1 h / 20 °C
5.1: 40 mg / pyridinium toluene-p-sulfonate / CH2Cl2 / 0.5 h / 20 °C
6.1: 36 percent / PhI(OAc)2; I2 / cyclohexane / 7 h / 20 °C / Irradiation
7.1: 53 percent / K2CO3 / methanol / 1.5 h / 20 °C
8.1: 80 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C
9.1: Mg / diethyl ether
9.2: 70 percent / diethyl ether / 2 h / Heating
10.1: dimethyldioxirane; K2CO3 / acetone / 1 h / 0 °C
With
dmap; n-butyllithium; tetrapropylammonium perruthennate; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; Amberlite resin IR 118; hydrogen; iodine; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; potassium carbonate; magnesium; 4-methylmorpholine N-oxide; triethylamine;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; ethyl acetate; acetone; pentane;
9.2: Barbier reaction;
DOI:10.1039/b008159k
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337533-69-4
(2R,4R,5R,7S,9S,10S,12R,1'R/S,4'S/R,5'S/R,1''S)-9-[1-(tert-Butyldiphenylsilyloxymethyl)propyl]-2-(4,5-epoxy-1-hydroxy-4-methylhexan-1-yl)-4,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: H2; K2CO3 / Lindlar catalyst / pentane; ethyl acetate / 1 h / 20 °C
2.1: 40 mg / pyridinium toluene-p-sulfonate / CH2Cl2 / 0.5 h / 20 °C
3.1: 36 percent / PhI(OAc)2; I2 / cyclohexane / 7 h / 20 °C / Irradiation
4.1: 53 percent / K2CO3 / methanol / 1.5 h / 20 °C
5.1: 80 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C
6.1: Mg / diethyl ether
6.2: 70 percent / diethyl ether / 2 h / Heating
7.1: dimethyldioxirane; K2CO3 / acetone / 1 h / 0 °C
With
tetrapropylammonium perruthennate; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; hydrogen; iodine; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; potassium carbonate; magnesium; 4-methylmorpholine N-oxide;
Lindlar's catalyst;
In
methanol; diethyl ether; dichloromethane; cyclohexane; ethyl acetate; acetone; pentane;
6.2: Barbier reaction;
DOI:10.1039/b008159k