Technology Process of (+)-(4S,5R,6R,7R)-6-benzyloxy-8-tert-butyldiphenylsilyloxy-3,3-dimethyl-4-methoxy-5,7-methylenedioxyoctyl-1-ene
There total 19 articles about (+)-(4S,5R,6R,7R)-6-benzyloxy-8-tert-butyldiphenylsilyloxy-3,3-dimethyl-4-methoxy-5,7-methylenedioxyoctyl-1-ene 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:
-
Methyltriphenylphosphonium bromide;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at 65 ℃;
for 0.25h;
(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal;
In
tetrahydrofuran; hexane;
at 0 ℃;
for 0.333333h;
DOI:10.1021/ol052943c
DOI:10.1021/jo060803q
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -30 °C
2.1: Yb(OTf)3 / CH2Cl2 / 48 h / 20 °C
3.1: NaH / tetrahydrofuran / 0 - 20 °C
3.2: 95 percent / tetrahydrofuran / 0 - 20 °C
4.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C
5.1: 97 percent / SO3*Py; Et3N / dimethylsulfoxide / 2.5 h
6.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 65 °C
6.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / 0 °C
With
n-butyllithium; oxalyl dichloride; pyridine-SO3 complex; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;
1.1: Swern oxidation / 6.2: Wittig reaction;
DOI:10.1021/jo060803q
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 61 percent / DMAP; Et3N / CH2Cl2 / 10 h / 20 °C
2.1: 98 percent / AcOH; H2O / tetrahydrofuran / 6 h / 55 °C
3.1: 89 percent / pyridine / CH2Cl2 / 10 h / 20 °C
4.1: 88 percent / P2O5 / CH2Cl2 / 1.5 h
5.1: 99 percent / DIBALH / tetrahydrofuran / 1 h / 0 °C
6.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -30 °C
7.1: Yb(OTf)3 / CH2Cl2 / 48 h / 20 °C
8.1: NaH / tetrahydrofuran / 0 - 20 °C
8.2: 95 percent / tetrahydrofuran / 0 - 20 °C
9.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C
10.1: 97 percent / SO3*Py; Et3N / dimethylsulfoxide / 2.5 h
11.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 65 °C
11.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / 0 °C
With
pyridine; dmap; n-butyllithium; oxalyl dichloride; pyridine-SO3 complex; water; phosphorus pentoxide; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;
6.1: Swern oxidation / 11.2: Wittig reaction;
DOI:10.1021/jo060803q
