Technology Process of (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-7-triethyl-silanyloxy-9-decene-1-ol
There total 8 articles about (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-7-triethyl-silanyloxy-9-decene-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate;
4 A molecular sieve;
In
decane; dichloromethane;
at -25 - -20 ℃;
for 14.5h;
DOI:10.1039/b308305e
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: CF3SO3H / diethyl ether / 0.17 h / 0 °C
2.1: 371 mg / TBAF / tetrahydrofuran / 1 h / 20 °C
3.1: 91 percent / pyridine; DMAP / 3 h / 25 °C
4.1: OsO4; aq. NMO / acetone / 12 h / 20 °C
5.1: 3.2 g / aq. NaIO4 / tetrahydrofuran / 0 °C / pH 7
6.1: 94 percent / BF3*Et2O / CH2Cl2 / 2 h / -78 °C
7.1: 2,6-lutidine / CH2Cl2 / -50 °C
8.1: 347 mg / DIBALH / toluene; hexane / 2 h / -78 °C
9.1: DMSO; (COCl)2; Et3N / CH2Cl2 / 1.5 h / -70 - -30 °C
10.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C
10.2: 309 mg / tetrahydrofuran / 1 h / -78 °C
11.1: 89 percent / DIBAL-H / toluene; hexane / 2 h / -78 °C
12.1: 98 percent / L-(+)-diethyl tartrate; Ti(i-OPr)4; t-BuOOH / 4 Angstroem molecular sieves / CH2Cl2; decane / 14.5 h / -25 - -20 °C
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diethyl (2R,3R)-tartrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
4 A molecular sieve;
In
tetrahydrofuran; diethyl ether; decane; hexane; dichloromethane; acetone; toluene;
10.2: Wadsworth-Emmons olefination / 12.1: Sharpless reaction;
DOI:10.1039/b308305e
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 347 mg / DIBALH / toluene; hexane / 2 h / -78 °C
2.1: DMSO; (COCl)2; Et3N / CH2Cl2 / 1.5 h / -70 - -30 °C
3.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C
3.2: 309 mg / tetrahydrofuran / 1 h / -78 °C
4.1: 89 percent / DIBAL-H / toluene; hexane / 2 h / -78 °C
5.1: 98 percent / L-(+)-diethyl tartrate; Ti(i-OPr)4; t-BuOOH / 4 Angstroem molecular sieves / CH2Cl2; decane / 14.5 h / -25 - -20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
4 A molecular sieve;
In
tetrahydrofuran; decane; hexane; dichloromethane; toluene;
3.2: Wadsworth-Emmons olefination / 5.1: Sharpless reaction;
DOI:10.1039/b308305e
