Technology Process of (2E,8Z,10E,16E,18E,20Z)-(S)-20-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methoxymethoxy-2-methyl-9-trimethylsilanyl-docosa-2,8,10,16,18,20-hexaenoic acid allyl ester
There total 15 articles about (2E,8Z,10E,16E,18E,20Z)-(S)-20-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methoxymethoxy-2-methyl-9-trimethylsilanyl-docosa-2,8,10,16,18,20-hexaenoic acid allyl ester 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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213122-60-2
(2E,8Z,10E,16E,18E,20Z)-(S)-20-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methoxymethoxy-2-methyl-9-trimethylsilanyl-docosa-2,8,10,16,18,20-hexaenoic acid allyl ester
- Guidance literature:
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Multi-step reaction with 4 steps
1: 85 percent / tetrahydrofuran / -40 - 25 °C
2: 1.) BrCl2CCCl2Br, PPh3 / 1.) CH2Cl2, 0 deg C, 2.) CH3CN, 70 deg C
3: 84 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 23 °C
4: 1.) LiBF4, H2O, 2.) LiCl, DBU / 1.) CH3CN, 2.) CH3CN
With
lithium tetrafluoroborate; n-butyllithium; 1,2-dibromo-1,1,2,2-tetrachloroethane; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium chloride;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
DOI:10.1021/ja980611f
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213122-60-2
(2E,8Z,10E,16E,18E,20Z)-(S)-20-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methoxymethoxy-2-methyl-9-trimethylsilanyl-docosa-2,8,10,16,18,20-hexaenoic acid allyl ester
- Guidance literature:
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Multi-step reaction with 10 steps
1: 70 percent / AlCl3
2: (-)-(α)-pinene, 9-BBN
3: i-Pr2NEt / 25 °C
4: DIBAL-H / CH2Cl2 / -78 °C
5: p-TsOH / methanol
6: 1.) DIBAL-H, 2.) NIS, pyridine / 1.) Et2O, 50 deg C
7: Pd(PPh3)4, TlOH / tetrahydrofuran; H2O
8: DMSO, (COCl)2 / CH2Cl2 / -78 °C
9: 84 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 23 °C
10: 1.) LiBF4, H2O, 2.) LiCl, DBU / 1.) CH3CN, 2.) CH3CN
With
pyridine; N-iodo-succinimide; lithium tetrafluoroborate; 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; aluminium trichloride; TlOH; oxalyl dichloride; water; diisobutylaluminium hydride; 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;
DOI:10.1021/ja980611f
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213122-60-2
(2E,8Z,10E,16E,18E,20Z)-(S)-20-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methoxymethoxy-2-methyl-9-trimethylsilanyl-docosa-2,8,10,16,18,20-hexaenoic acid allyl ester
- Guidance literature:
-
Multi-step reaction with 3 steps
1: 1.) BrCl2CCCl2Br, PPh3 / 1.) CH2Cl2, 0 deg C, 2.) CH3CN, 70 deg C
2: 84 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 23 °C
3: 1.) LiBF4, H2O, 2.) LiCl, DBU / 1.) CH3CN, 2.) CH3CN
With
lithium tetrafluoroborate; n-butyllithium; 1,2-dibromo-1,1,2,2-tetrachloroethane; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium chloride;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
DOI:10.1021/ja980611f