(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Base Information

Chemical Name:(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane
CAS No.:944740-57-2
Molecular Formula:C₄₃H₆₈O₈Si
Molecular Weight:741.094
Hs Code.:

(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Synonyms:(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

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Chemical Property of (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

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Technology Process of (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

There total 9 articles about (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane 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: 90.0%

: 64761-29-1
mesitaldehyde dimethylacetal

: 608143-14-2
(2S,3R,4R,6R,7S,8S,9R,10R,11R)-11-(benzyloxymethoxy)-1-O-tert-butyldimethylsilyl-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyldecane-1,7,9-triol

: 944740-57-2
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Guidance literature:: With (+)-10-camphorsulfonic acid; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: (4R,6R,7R,8S)-9-[(tert-butyldimethylsilyl)oxy]-6,7-(carbonyldioxy)-4,6,8-trimethylnonan-3-one

: 944740-57-2
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 °C

1.2: 83 percent / tetrahydrofuran / 2 h / -78 - -20 °C

2.1: 93 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 12 h / -25 - -20 °C

3.1: 90 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

With acetic acid; (+)-10-camphorsulfonic acid; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: 123163-78-0
(2S,3R)-3-<(benzyloxy)methoxy>-2-methylpentanal

: 944740-57-2
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 °C

1.2: 83 percent / tetrahydrofuran / 2 h / -78 - -20 °C

2.1: 93 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 12 h / -25 - -20 °C

3.1: 90 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

With acetic acid; (+)-10-camphorsulfonic acid; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2007.02.044