Technology Process of (2R,4E,6R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-4,11,17-trien-3-one
There total 45 articles about (2R,4E,6R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-4,11,17-trien-3-one 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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(7Z,13E)-(2R,4S,5R,6S,9S,11S,12R)-5,9,11-Tris-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-15-trityloxy-pentadeca-7,13-dienal
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792921-67-6
(2R,4E,6R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-4,11,17-trien-3-one
- Guidance literature:
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{3(R)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-2-oxobutyl}phosphonic acid dimethyl ester;
With
barium dihydroxide;
In
tetrahydrofuran;
at 20 ℃;
for 0.5h;
(7Z,13E)-(2R,4S,5R,6S,9S,11S,12R)-5,9,11-Tris-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-15-trityloxy-pentadeca-7,13-dienal;
In
tetrahydrofuran;
at 20 ℃;
for 12h;
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792921-67-6
(2R,4E,6R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-4,11,17-trien-3-one
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C
1.2: 93 percent / tetrahydrofuran; hexane / -78 - 0 °C
2.1: 79 percent / i-PrOH / (S,S)-Noyori catalyst
3.1: 91 percent / hydrogen / Lindlar catalyst / toluene / 1 h
4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5.1: 67 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 21 h / 0 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 1 h
7.1: activated Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C
7.2: 2.60 g / tetrahydrofuran; H2O / 12 h
With
pyridine; 2,6-dimethylpyridine; barium dihydroxide; n-butyllithium; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; isopropyl alcohol;
Lindlar's catalyst; (S,S)-Noyori catalyst;
In
tetrahydrofuran; hexane; dichloromethane; toluene;
6.1: Dess-Martin oxidation / 7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033
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792921-67-6
(2R,4E,6R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-4,11,17-trien-3-one
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: 100 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating
2.1: 89 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C
3.1: sulfur trioxide*pyridine complex; Et3N; DMSO / CH2Cl2 / 0 - 20 °C
4.1: 2-methyl-2-butene; NaH2PO4*H2O; NaClO2 / H2O; tetrahydrofuran / 2 h
5.1: 2.65 g / 4-(dimethylamino)pyridine; Et3N; DCC / CH2Cl2 / 0 - 20 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C
6.2: 93 percent / tetrahydrofuran; hexane / -78 - 0 °C
7.1: 79 percent / i-PrOH / (S,S)-Noyori catalyst
8.1: 91 percent / hydrogen / Lindlar catalyst / toluene / 1 h
9.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
10.1: 67 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 21 h / 0 °C
11.1: Dess-Martin periodinane / CH2Cl2 / 1 h
12.1: activated Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C
12.2: 2.60 g / tetrahydrofuran; H2O / 12 h
With
pyridine; 2,6-dimethylpyridine; dmap; barium dihydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; isopropyl alcohol;
Lindlar's catalyst; (S,S)-Noyori catalyst;
In
tetrahydrofuran; hexane; dichloromethane; water; toluene;
11.1: Dess-Martin oxidation / 12.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033
