Technology Process of (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-hydroxy-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane
There total 12 articles about (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-hydroxy-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane 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 8 steps
1: imidazole
2: OsO4, Pb(OAc)4
3: 95 percent / n-Bu2BOTf, i-Pr2NEt / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) -78 deg C to r.t., 5 h
4: AlMe3 / toluene / 1.) 0 deg C - r.t., 1 h, 2.) 0 deg C - r.t., overnight
5: imidazole / dimethylformamide
6: 87 percent / DIBAL-H / toluene / 0.17 h / -78 °C
7: 1.) Bu3SnH, AIBN, 2.) MgBr2*OEt2 / 1.) toluene, 90 deg C, 2 h, 2.) CH2Cl2, 0 deg C, 1 h; -23 deg C to r.t., 5 h
8: 1.) 9-BBN, 2.) H2O2 / 1.) THF, sonicate, 90 min
With
1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; 2,2'-azobis(isobutyronitrile); di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; magnesium bromide;
In
dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00090a032
- Guidance literature:
-
Multi-step reaction with 3 steps
1: 90 percent / n-BuLi, TMEDA / tetrahydrofuran; hexane / 1.) 30 min, 2.) 1 h
2: 1.) Bu3SnH, AIBN, 2.) MgBr2*OEt2 / 1.) toluene, 90 deg C, 2 h, 2.) CH2Cl2, 0 deg C, 1 h; -23 deg C to r.t., 5 h
3: 1.) 9-BBN, 2.) H2O2 / 1.) THF, sonicate, 90 min
With
9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; dihydrogen peroxide; tri-n-butyl-tin hydride; magnesium bromide;
In
tetrahydrofuran; hexane;
DOI:10.1021/jo00090a032
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 95 percent / triflic acid / CH2Cl2 / 0.5 h / Ambient temperature
2: 85 percent / LiAlH4 / diethyl ether / 0.5 h
3: 88 percent / DMAP, pyridine / 3 h / Ambient temperature
4: 98 percent / NaI / acetone / 48 h
5: 90 percent / n-BuLi, TMEDA / tetrahydrofuran; hexane / 1.) 30 min, 2.) 1 h
6: 1.) Bu3SnH, AIBN, 2.) MgBr2*OEt2 / 1.) toluene, 90 deg C, 2 h, 2.) CH2Cl2, 0 deg C, 1 h; -23 deg C to r.t., 5 h
7: 1.) 9-BBN, 2.) H2O2 / 1.) THF, sonicate, 90 min
With
pyridine; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; trifluorormethanesulfonic acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium iodide; magnesium bromide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone;
DOI:10.1021/jo00090a032
