Technology Process of (4R,5R)-(+)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(2Z-octenyl)-α-[(1R,2R)-1,2-epoxy-6-(4-methoxyphenylmethoxy)hexyl]cyclopent-2-enemethanol
There total 18 articles about (4R,5R)-(+)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(2Z-octenyl)-α-[(1R,2R)-1,2-epoxy-6-(4-methoxyphenylmethoxy)hexyl]cyclopent-2-enemethanol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(3S,4R)-(+)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)cyclopent-1-ene;
With
tert.-butyl lithium;
In
diethyl ether; pentane;
at -78 ℃;
for 1h;
(2S,3R)-3-[4-(4-methoxyphenylmethoxy)butyl]oxirane-2-carboxaldehyde;
In
diethyl ether; pentane;
at -78 ℃;
for 0.75h;
DOI:10.1021/ol051415y
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 94 percent / TMSOTf / acetonitrile / 0.5 h / -23 °C
2.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 22 °C
3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C
3.2: 91 percent / tetrahydrofuran / 0.33 h / 22 °C
4.1: 100 percent / diisobutylaluminum hydride / cyclohexane; CH2Cl2 / 0.33 h / -78 °C
5.1: 94 percent / titanium tetraisopropoxide; tert-butyl hydroperoxide; molecular sieves 4 Angstroem / D-(-)-diisopropyl tartrate / CH2Cl2; decane / -20 - 0 °C
6.1: pyridine; Dess-Martin periodinane / benzene; acetonitrile / 0.67 h / 22 °C
7.1: tert-butyllithium / pentane; diethyl ether / 1 h / -78 °C
7.2: 75 percent / pentane; diethyl ether / 0.75 h / -78 °C
With
pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine;
D-(-)-diisopropyl tartrate;
In
tetrahydrofuran; diethyl ether; decane; dichloromethane; cyclohexane; acetonitrile; pentane; benzene;
2.1: Swern oxidation / 3.2: Horner-Emmons reaction / 5.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol051415y
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 22 °C
2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C
2.2: 91 percent / tetrahydrofuran / 0.33 h / 22 °C
3.1: 100 percent / diisobutylaluminum hydride / cyclohexane; CH2Cl2 / 0.33 h / -78 °C
4.1: 94 percent / titanium tetraisopropoxide; tert-butyl hydroperoxide; molecular sieves 4 Angstroem / D-(-)-diisopropyl tartrate / CH2Cl2; decane / -20 - 0 °C
5.1: pyridine; Dess-Martin periodinane / benzene; acetonitrile / 0.67 h / 22 °C
6.1: tert-butyllithium / pentane; diethyl ether / 1 h / -78 °C
6.2: 75 percent / pentane; diethyl ether / 0.75 h / -78 °C
With
pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; 4 A molecular sieve; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine;
D-(-)-diisopropyl tartrate;
In
tetrahydrofuran; diethyl ether; decane; dichloromethane; cyclohexane; acetonitrile; pentane; benzene;
1.1: Swern oxidation / 2.2: Horner-Emmons reaction / 4.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol051415y
![(2S,3R)-3-[4-(4-methoxyphenylmethoxy)butyl]oxirane-2-carboxaldehyde](/Databaselist/images/loading.webp)
