Technology Process of (2R,3R,4S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6-trimethylheptanal
There total 10 articles about (2R,3R,4S,6S,7S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6-trimethylheptanal 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:
-
(3S,4S,5S,6S,7S)-4-O-methyl-6-O-(tert-butyldimethylsilyl)-8-O-(tert-butyldiphenylsilyl)-3,5,7-trimethyl-1-octen-4,6,8-triol;
With
osmium(VIII) oxide; N-methyl-2-indolinone; water;
In
acetone;
at 20 ℃;
With
water;
In
acetone;
for 0.5h;
DOI:10.1016/S0957-4166(03)00372-0
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: Bu2BOTf; Et3N / CH2Cl2 / 1.5 h / -78 - 0 °C
1.2: 98 percent / CH2Cl2 / 2 h / -78 - -10 °C
2.1: 97 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 - 20 °C
3.1: 75 percent / LiBH4 / methanol; tetrahydrofuran / 1 h / 0 °C
4.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
5.1: tert-BuOK; n-BuLi; (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / -78 - -45 °C
5.2: BF3*Et2O / tetrahydrofuran; hexane / 4 h / -78 °C
5.3: 220 mg / aq. NaOH; H2O2 / tetrahydrofuran; hexane / 25 °C
6.1: 78 percent / 2,6-di-tert-butylpyridine / CH2Cl2 / 14 h / 0 - 20 °C
7.1: OsO4; NMO; H2O / acetone / 20 °C
7.2: HIO6; H2O / acetone / 0.5 h
With
(+)-Ipc2BOMe; 2,6-dimethylpyridine; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; water; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; acetone;
4.1: Swern oxidation;
DOI:10.1016/S0957-4166(03)00372-0
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 0 °C
2.1: Bu2BOTf; Et3N / CH2Cl2 / 1.5 h / -78 - 0 °C
2.2: 98 percent / CH2Cl2 / 2 h / -78 - -10 °C
3.1: 97 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 - 20 °C
4.1: 75 percent / LiBH4 / methanol; tetrahydrofuran / 1 h / 0 °C
5.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
6.1: tert-BuOK; n-BuLi; (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / -78 - -45 °C
6.2: BF3*Et2O / tetrahydrofuran; hexane / 4 h / -78 °C
6.3: 220 mg / aq. NaOH; H2O2 / tetrahydrofuran; hexane / 25 °C
7.1: 78 percent / 2,6-di-tert-butylpyridine / CH2Cl2 / 14 h / 0 - 20 °C
8.1: OsO4; NMO; H2O / acetone / 20 °C
8.2: HIO6; H2O / acetone / 0.5 h
With
(+)-Ipc2BOMe; 2,6-dimethylpyridine; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; water; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; acetone;
1.1: Swern oxidation / 5.1: Swern oxidation;
DOI:10.1016/S0957-4166(03)00372-0
