Technology Process of (E)-(2R,3S,4S)-4-O-acetyl-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-octen-7-one-1,2,3,4-tetraol
There total 9 articles about (E)-(2R,3S,4S)-4-O-acetyl-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-octen-7-one-1,2,3,4-tetraol 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
camphor-10-sulfonic acid;
In
water; acetone;
for 1h;
Yield given;
Ambient temperature;
DOI:10.1021/ja00247a025
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 1.) butyllithium 2.) ZnBr2 / tetrahydrofuran; hexane / 1.) from -30 deg C to 10 deg C, 4 h 2.) 15 min 3.) -40 deg C, 4 h, then to 0 deg C, within 3 h
2: 91 percent / imidazole / dimethylformamide / 5 h / 80 °C
3: 82 percent / pyridine, bromine / acetonitrile; H2O / 1.) -20 deg C 2.) rt, 2 h
4: 82 percent / camphorsulfonic acid / methanol / 0 °C
5: 77 percent / DIBAL / diethyl ether / 0.5 h / -78 °C
6: Et3N, DMAP / CH2Cl2 / 5 h / Ambient temperature
7: CSA / acetone; H2O / 1 h / Ambient temperature
With
pyridine; 1H-imidazole; dmap; n-butyllithium; camphor-10-sulfonic acid; bromine; diisobutylaluminium hydride; triethylamine; zinc dibromide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja00247a025
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 91 percent / imidazole / dimethylformamide / 5 h / 80 °C
2: 82 percent / pyridine, bromine / acetonitrile; H2O / 1.) -20 deg C 2.) rt, 2 h
3: 82 percent / camphorsulfonic acid / methanol / 0 °C
4: 77 percent / DIBAL / diethyl ether / 0.5 h / -78 °C
5: Et3N, DMAP / CH2Cl2 / 5 h / Ambient temperature
6: CSA / acetone; H2O / 1 h / Ambient temperature
With
pyridine; 1H-imidazole; dmap; camphor-10-sulfonic acid; bromine; diisobutylaluminium hydride; triethylamine;
In
methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja00247a025
![Acetic acid (E)-(S)-1-[(S)-(tert-butyl-diphenyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-4,4-dimethoxy-pent-2-enyl ester](/Databaselist/images/loading.webp)
