Technology Process of (3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate
There total 31 articles about (3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate 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:
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![(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-(allyloxy)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate](/Databaselist/images/loading.webp)
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935872-07-4
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-(allyloxy)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate
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935872-03-0
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate
- Guidance literature:
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With
N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve;
In
dichloromethane;
at 20 ℃;
for 1.5h;
DOI:10.1021/jo062089i
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935872-03-0
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate
- Guidance literature:
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Multi-step reaction with 14 steps
1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C
2: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C
3: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C
4: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
5: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
6: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
7: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
8: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
9: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
10: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
11: Et3N / benzene / 1 h / 20 °C
12: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
13: 96 percent / PPTS / ethanol / 16 h / 50 °C
14: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
With
2,6-dimethylpyridine; dmap; lithium hydroxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; ammonium formate; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
tetrakis(triphenylphosphine) palladium(0); {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF4;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; benzene;
DOI:10.1021/jo062089i
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935872-03-0
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate
- Guidance literature:
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Multi-step reaction with 11 steps
1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
2: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
3: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
4: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
5: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
6: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
8: Et3N / benzene / 1 h / 20 °C
9: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
10: 96 percent / PPTS / ethanol / 16 h / 50 °C
11: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
With
2,6-dimethylpyridine; dmap; lithium hydroxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; triethylamine;
{(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF4;
In
tetrahydrofuran; ethanol; dichloromethane; benzene;
DOI:10.1021/jo062089i
