Technology Process of (1R,2S,3S,5S,6R,7S)-4,10-dioxa-3-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxy]-5-[(3',4',5')-trimethoxyphenyl]-tricyclo[5.2.1.02,6]dec-8-en-3-ol
There total 10 articles about (1R,2S,3S,5S,6R,7S)-4,10-dioxa-3-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxy]-5-[(3',4',5')-trimethoxyphenyl]-tricyclo[5.2.1.02,6]dec-8-en-3-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
1-bromo-3-methoxy-4-propoxy-5-(2'-tert-butyldimethylsilyloxyethanesulfanyl)benzene;
With
tert.-butyl lithium;
In
pentane;
at -78 ℃;
for 0.5h;
(1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-one;
In
tetrahydrofuran; pentane;
at -78 ℃;
for 0.5h;
DOI:10.1016/S0957-4166(02)00334-8
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 96 percent / cesium carbonate / dimethylformamide / 2 h / 50 °C
2.1: 91 percent / 2-methyl-2-butene; aq. sodium chlorite; NaH2PO4 / 2-methyl-propan-2-ol / 4 h / 20 °C
3.1: oxalyl chloride / dimethylformamide; CH2Cl2 / 18 h / 20 °C
4.1: 1.6 g / 2-mercaptopyridine oxide sodium salt; BrCCl3; AIBN / 0.08 h / Heating
5.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 °C
6.1: 92 percent / imidazole / dimethylformamide / 20 °C
7.1: t-BuLi / pentane / 0.5 h / -78 °C
7.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C
With
1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; tert.-butyl lithium; 2-mercaptopyridine-1-oxide sodium salt; copper; caesium carbonate;
In
dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;
DOI:10.1016/S0957-4166(02)00334-8
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C
1.2: ClTi(O-i-Pr)3 / diethyl ether; pentane; hexane / -40 - 0 °C
1.3: 91 percent / tetrahydrofuran; diethyl ether; various solvents / 4.5 h / 0 - 20 °C
2.1: 78 percent / 4 Angstroem molecular sieves; 4-methoxymorpholine N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 5 h / 20 °C
3.1: t-BuLi / pentane / 0.5 h / -78 °C
3.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C
With
tetrapropylammonium perruthennate; NMO; 4 A molecular sieve; tert.-butyl lithium;
In
diethyl ether; dichloromethane; pentane;
DOI:10.1016/S0957-4166(02)00334-8