Technology Process of (3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene
There total 15 articles about (3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene 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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944740-76-5
(3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadec-1-en-4-ol
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188786-19-8
(3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene
- Guidance literature:
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With
3 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
dichloromethane;
at 20 ℃;
for 0.5h;
DOI:10.1016/j.tet.2007.02.044
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188786-19-8
(3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C
1.2: 86 percent / tetrahydrofuran / 1 h / -78 °C
2.1: 73 percent / acetic acid; Me4NBH4 / acetonitrile / 70 h / -10 - -6 °C
3.1: 83 percent / (+)-10-camphorsulfonic acid / CH2Cl2 / 3 h / 20 °C
4.1: 88 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 40 h / 20 °C
5.1: 96 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; pyridine / CH2Cl2 / 2 h / 20 °C
6.1: 69 percent / BF3*OEt2 / CH2Cl2 / 5 h / -78 °C
7.1: 91 percent / molecular sieves 3 Angstroem; DDQ / CH2Cl2 / 0.5 h / 20 °C
With
pyridine; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetramethylammonium borohydride; Dess-Martin periodane; acetic acid; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; dichloromethane; acetonitrile;
5.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.02.044
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188786-19-8
(3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: 85 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.25 h / 20 °C
2.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C
2.2: 86 percent / tetrahydrofuran / 1 h / -78 °C
3.1: 73 percent / acetic acid; Me4NBH4 / acetonitrile / 70 h / -10 - -6 °C
4.1: 83 percent / (+)-10-camphorsulfonic acid / CH2Cl2 / 3 h / 20 °C
5.1: 88 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 40 h / 20 °C
6.1: 96 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; pyridine / CH2Cl2 / 2 h / 20 °C
7.1: 69 percent / BF3*OEt2 / CH2Cl2 / 5 h / -78 °C
8.1: 91 percent / molecular sieves 3 Angstroem; DDQ / CH2Cl2 / 0.5 h / 20 °C
With
pyridine; mercury(II) perchlorate; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetramethylammonium borohydride; Dess-Martin periodane; acetic acid; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; lithium hexamethyldisilazane;
In
tetrahydrofuran; dichloromethane; water; acetonitrile;
6.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.02.044