Technology Process of 1-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}hexa-1(E),5-dien-3(R)-ol
There total 11 articles about 1-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}hexa-1(E),5-dien-3(R)-ol 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:
-
allylmagnesium bromide;
With
(+)-Ipc2BOMe;
In
diethyl ether;
at -78 - 23 ℃;
for 1.5h;
3-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolane-4(R)-yl}prop-2(E)-enal;
With
dihydrogen peroxide;
In
diethyl ether;
at -100 ℃;
for 1h;
With
dihydrogen peroxide;
In
tetrahydrofuran; diethyl ether; ethanol;
at 20 ℃;
for 12h;
pH=7;
Further stages.;
DOI:10.1021/ol025537r
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 88 percent / imidazole / CH2Cl2 / 4 h / 23 °C
2.1: OsO4; N-methylmorpholine N-oxide / acetone; H2O / 4 h / 20 °C
2.2: 64 percent / NaIO4/SiO2 / CH2Cl2 / 2 h / 23 °C
3.1: 87 percent / benzene / 12 h / 23 °C
4.1: AD-mix-β / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
4.2: 3.63 g / PPTS / CH2Cl2 / 8 h / 23 °C
5.1: 82 percent / N-bromosuccinimide; AgNO3 / acetone / 2 h / 23 °C
6.1: 85 percent / (KO2CN=)2; AcOH / tetrahydrofuran / 24 h / 23 °C
7.1: 83 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 23 °C
8.1: 86 percent / (ClCO)2; DMSO; Et3N / 2 h / -78 - 0 °C
9.1: 88 percent / CH2Cl2 / 8 h / 40 °C
10.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / 1.5 h / -78 - 23 °C
10.2: H2O2 / diethyl ether / 1 h / -100 °C
10.3: 82 percent / aq.H2O2 / diethyl ether; ethanol; tetrahydrofuran / 12 h / 20 °C / pH 7
With
(+)-Ipc2BOMe; 1H-imidazole; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; AD-mix-β; potassium diazodicarboxylate; silver nitrate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
4.1: Sharpless asymmetric dihydroxylation / 8.1: Swern oxidation;
DOI:10.1021/ol025537r
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 88 percent / imidazole / CH2Cl2 / 4 h / 23 °C
2.1: OsO4; N-methylmorpholine N-oxide / acetone; H2O / 4 h / 20 °C
2.2: 64 percent / NaIO4/SiO2 / CH2Cl2 / 2 h / 23 °C
3.1: 87 percent / benzene / 12 h / 23 °C
4.1: AD-mix-β / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
4.2: 3.63 g / PPTS / CH2Cl2 / 8 h / 23 °C
5.1: 82 percent / N-bromosuccinimide; AgNO3 / acetone / 2 h / 23 °C
6.1: 85 percent / (KO2CN=)2; AcOH / tetrahydrofuran / 24 h / 23 °C
7.1: 83 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 - 23 °C
8.1: 86 percent / (ClCO)2; DMSO; Et3N / 2 h / -78 - 0 °C
9.1: 88 percent / CH2Cl2 / 8 h / 40 °C
10.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / 1.5 h / -78 - 23 °C
10.2: H2O2 / diethyl ether / 1 h / -100 °C
10.3: 82 percent / aq.H2O2 / diethyl ether; ethanol; tetrahydrofuran / 12 h / 20 °C / pH 7
With
(+)-Ipc2BOMe; 1H-imidazole; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; AD-mix-β; potassium diazodicarboxylate; silver nitrate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
4.1: Sharpless asymmetric dihydroxylation / 8.1: Swern oxidation;
DOI:10.1021/ol025537r
