(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

Base Information

Chemical Name:(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
CAS No.:944740-76-5
Molecular Formula:C₅₄H₈₄O₈Si
Molecular Weight:889.342
Hs Code.:

(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

Synonyms:(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

Suppliers and Price of (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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Chemical Property of (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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Technology Process of (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

There total 15 articles about (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 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:

Reference yield: 69.0%

: 31197-41-8,76505-19-6
crotyltributylstannane

: 188786-14-3
(2R,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-4-[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecanal

: (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

: 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

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 5h;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: 188785-99-1
(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonan-7-one

: 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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetramethylammonium borohydride; Dess-Martin periodane; acetic acid; (+)-10-camphorsulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetonitrile; 5.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: 188785-95-7
(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane

: 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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; mercury(II) perchlorate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetramethylammonium borohydride; Dess-Martin periodane; acetic acid; (+)-10-camphorsulfonic acid; calcium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetonitrile; 6.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.02.044