Technology Process of (1S,4S,5S,6R)-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octan-2-one
There total 14 articles about (1S,4S,5S,6R)-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octan-2-one 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:
-
Multi-step reaction with 11 steps
1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
2.1: tBuOK / tetrahydrofuran / 0.5 h / -42 °C
3.1: 12.7 g / DIBAL-H / toluene; hexane / 0.5 h / -78 °C
4.1: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH2Cl2 / 5 h / -20 °C
5.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C
6.1: TBAF / tetrahydrofuran / 1 h / 20 °C
7.1: 3.89 g / DMAP / CH2Cl2 / 0.25 h / 0 °C
8.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
8.2: 99 percent / tetrahydrofuran / -78 - 20 °C
9.1: OsO4; NaIO4 / dioxane; H2O / 24 h
10.1: 2.40 g / Jones reagent / acetone / 0.17 h / 0 °C
11.1: 91 percent / NaH2PO4; Na-Hg / methanol / 0.5 h / 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; jones reagent; sodium amalgam; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
1.1: Oxidation / 2.1: Horner-Emmons reaction / 3.1: Reduction / 4.1: Epoxidation / 5.1: Alkylation / 6.1: desilylation / 7.1: mesylation / 8.1: Metallation / 8.2: Cyclization / 9.1: Oxidation / 10.1: Oxidation / 11.1: Reduction;
DOI:10.1016/S0040-4020(00)00730-4
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: tBuOK / tetrahydrofuran / 0.5 h / -42 °C
2.1: 12.7 g / DIBAL-H / toluene; hexane / 0.5 h / -78 °C
3.1: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH2Cl2 / 5 h / -20 °C
4.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C
5.1: TBAF / tetrahydrofuran / 1 h / 20 °C
6.1: 3.89 g / DMAP / CH2Cl2 / 0.25 h / 0 °C
7.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
7.2: 99 percent / tetrahydrofuran / -78 - 20 °C
8.1: OsO4; NaIO4 / dioxane; H2O / 24 h
9.1: 2.40 g / Jones reagent / acetone / 0.17 h / 0 °C
10.1: 91 percent / NaH2PO4; Na-Hg / methanol / 0.5 h / 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; jones reagent; sodium amalgam; diethyl (2S,3S)-tartrate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
1.1: Horner-Emmons reaction / 2.1: Reduction / 3.1: Epoxidation / 4.1: Alkylation / 5.1: desilylation / 6.1: mesylation / 7.1: Metallation / 7.2: Cyclization / 8.1: Oxidation / 9.1: Oxidation / 10.1: Reduction;
DOI:10.1016/S0040-4020(00)00730-4
![(3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one](/Databaselist/images/loading.webp)
