Technology Process of (1S,3S,5S,6S)-3-Methoxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane
There total 1 articles about (1S,3S,5S,6S)-3-Methoxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
silver(l) oxide;
In
acetonitrile;
at 23 ℃;
for 14h;
DOI:10.1021/ol026260y
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 94 percent / Na; NH3 / tetrahydrofuran / 0.5 h / -78 °C
2.1: (COCl)2; DMSO / CH2Cl2 / 1.5 h / -78 °C
2.2: 90 percent / Et3N / CH2Cl2 / 0.33 h / 0 °C
3.1: NaH2PO4*2H2O; NaClO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 23 °C
4.1: 100 mg / diethyl ether / 2 h / 0 °C
5.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
5.2: PhSeCl / tetrahydrofuran; toluene / 0.33 h / -78 °C
5.3: 73 percent / pyridine; H2O2 / CH2Cl2 / 1.5 h / 0 °C
6.1: 72 percent / DIBAL-H / diethyl ether; hexane / 1.5 h / -78 °C
7.1: 93 percent / DCC; DMAP / CH2Cl2 / 3 h / 23 °C
8.1: KHMDS; TMSCl; Et3N / toluene / 6.5 h / -85 - 70 °C
9.1: 79 mg / diethyl ether / 2 h / 0 °C
With
dmap; sodium dihydrogenphosphate; chloro-trimethyl-silane; 2-methyl-but-2-ene; oxalyl dichloride; sodium perchlorate; ammonia; sodium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; tert-butyl alcohol;
2.1: Swen oxidation / 8.1: Ireland-Claisen rearrangement;
DOI:10.1021/ol026260y
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 94 percent / Na; NH3 / tetrahydrofuran / 0.5 h / -78 °C
2.1: (COCl)2; DMSO / CH2Cl2 / 1.5 h / -78 °C
2.2: 90 percent / Et3N / CH2Cl2 / 0.33 h / 0 °C
3.1: NaH2PO4*2H2O; NaClO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 23 °C
4.1: 100 mg / diethyl ether / 2 h / 0 °C
5.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
5.2: PhSeCl / tetrahydrofuran; toluene / 0.33 h / -78 °C
5.3: 73 percent / pyridine; H2O2 / CH2Cl2 / 1.5 h / 0 °C
6.1: 72 percent / DIBAL-H / diethyl ether; hexane / 1.5 h / -78 °C
7.1: 93 percent / DCC; DMAP / CH2Cl2 / 3 h / 23 °C
With
dmap; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; sodium perchlorate; ammonia; sodium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; tert-butyl alcohol;
2.1: Swen oxidation;
DOI:10.1021/ol026260y
![(1S,5S,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-ol](/Databaselist/images/loading.webp)
