Technology Process of (3S,4S,5R,6S,8R)-5-benzyloxymethyl-8-(tert-butyldimethylsilyloxy)-5-methyl-4-vinyl-1-oxaspiro[2.5]octan-6-ol
There total 12 articles about (3S,4S,5R,6S,8R)-5-benzyloxymethyl-8-(tert-butyldimethylsilyloxy)-5-methyl-4-vinyl-1-oxaspiro[2.5]octan-6-ol which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
With
pyridine;
In
tetrahydrofuran; benzene;
at -78 - 20 ℃;
DOI:10.1021/jo050039s
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: potassium tert-butoxide / toluene / 3 h / Heating
1.2: 2.06 g / toluene / 2 h / 20 °C
2.1: 85 percent / selenium dioxide; tert-butyl hydroperoxide; salicylic acid / CH2Cl2; H2O / 72 h / Heating
3.1: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C
4.1: 80 percent / OsO4; sodium metaperiodate / tetrahydrofuran; H2O / 6 h / 20 °C
5.1: 90 percent / NaBH4 / methanol / 0.5 h / -78 - 0 °C
6.1: 75 percent / m-CPBA / CH2Cl2; H2O / 120 h / 37 °C
7.1: 88 percent / NaH; Bu4NI / tetrahydrofuran / 12 h / 20 °C
8.1: diisobutylaluminum hydride / toluene / 0.33 h / -80 °C
9.1: 592 mg / pyridine / benzene; tetrahydrofuran / -78 - 20 °C
With
pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; selenium(IV) oxide; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; salicylic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
1.2: Wittig olefination / 9.1: Tebbe olefination;
DOI:10.1021/jo050039s
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 85 percent / selenium dioxide; tert-butyl hydroperoxide; salicylic acid / CH2Cl2; H2O / 72 h / Heating
2: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C
3: 80 percent / OsO4; sodium metaperiodate / tetrahydrofuran; H2O / 6 h / 20 °C
4: 90 percent / NaBH4 / methanol / 0.5 h / -78 - 0 °C
5: 75 percent / m-CPBA / CH2Cl2; H2O / 120 h / 37 °C
6: 88 percent / NaH; Bu4NI / tetrahydrofuran / 12 h / 20 °C
7: diisobutylaluminum hydride / toluene / 0.33 h / -80 °C
8: 592 mg / pyridine / benzene; tetrahydrofuran / -78 - 20 °C
With
pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; selenium(IV) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; salicylic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
8: Tebbe olefination;
DOI:10.1021/jo050039s
