Technology Process of (2S,3R)-3-[(1R,2R,3S,4R,5R)-3,4-Bis-benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-1,5-dimethyl-5-triethylsilanyloxy-undecyl]-2-methyl-oxirane-2-carbaldehyde
There total 29 articles about (2S,3R)-3-[(1R,2R,3S,4R,5R)-3,4-Bis-benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-1,5-dimethyl-5-triethylsilanyloxy-undecyl]-2-methyl-oxirane-2-carbaldehyde 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
1-methyl-pyrrolidin-2-one; tetrapropylammonium perruthennate;
In
dichloromethane;
DOI:10.1016/j.tetlet.2005.06.079
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: NaH / tetrahydrofuran
1.2: DIBAL-H / CH2Cl2; tetrahydrofuran
2.1: 20 percent / Ti(O-iPr)4; D-(-)-DET; t-butylhydroperoxide / CH2Cl2
3.1: 87 percent / CuCN / diethyl ether / 8 h / 0 °C
4.1: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 7 h / 20 °C
5.1: 64 percent / DIBAL-H / toluene / 8 h / 0 °C
6.1: 98.1 mg / Dess Martin periodinane; NaHCO3 / CH2Cl2 / 4 h / 20 °C
7.1: 101 mg / benzene / 18 h / 100 °C
8.1: 100 percent / LiBH4 / tetrahydrofuran / 3.5 h / 20 °C
9.1: 75 percent / mCPBA; NaHCO3 / CH2Cl2 / 1 h / -22 °C
10.1: 237 mg / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 1.5 h / 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium borohydride; tetrapropylammonium perruthennate; diethyl (2S,3S)-tartrate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;
pyridinium p-toluenesulfonate;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene; benzene;
6.1: Dess Martin oxidation / 7.1: Wittig reaction / 9.1: Miyashita epoxidation;
DOI:10.1246/bcsj.79.468
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 100 percent / N-methylmorpholine N-oxide / OsO4 / acetone; H2O; 2-methyl-propan-2-ol / 40 h / 0 - 20 °C
2: 100 percent / LiBH4 / tetrahydrofuran / 2 h / 0 °C
3: 81 percent / benzene / 1.5 h / 20 °C
4: 515 mg / 4-(dimethylamino)pyridine / pyridine / 12 h / 20 °C
5: 424 mg / NaOMe / methanol; tetrahydrofuran / 4 h / 0 °C
6: 87 percent / CuCN / diethyl ether / 8 h / 0 °C
7: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 7 h / 20 °C
8: 64 percent / DIBAL-H / toluene / 8 h / 0 °C
9: 98.1 mg / Dess Martin periodinane; NaHCO3 / CH2Cl2 / 4 h / 20 °C
10: 101 mg / benzene / 18 h / 100 °C
11: 100 percent / LiBH4 / tetrahydrofuran / 3.5 h / 20 °C
12: 75 percent / mCPBA; NaHCO3 / CH2Cl2 / 1 h / -22 °C
13: 237 mg / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 1.5 h / 20 °C
With
dmap; lithium borohydride; tetrapropylammonium perruthennate; sodium methylate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;
osmium(VIII) oxide; pyridinium p-toluenesulfonate;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene;
9: Dess Martin oxidation / 10: Wittig reaction / 12: Miyashita epoxidation;
DOI:10.1246/bcsj.79.468
![{(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol](/Databaselist/images/loading.webp)
