(2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one

Base Information

Chemical Name:(2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one
CAS No.:149820-11-1
Molecular Formula:C₃₃H₅₆O₈Si
Molecular Weight:608.888
Hs Code.:

Synonyms:(2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one

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Chemical Property of (2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one

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Technology Process of (2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one

There total 7 articles about (2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-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:

Reference yield: 83.0%

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

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

: 149820-11-1
(2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one

Guidance literature:: (4R,6R,7R,8S)-9-[(tert-butyldimethylsilyl)oxy]-6,7-(carbonyldioxy)-4,6,8-trimethylnonan-3-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

(2S,3R)-3-<(benzyloxy)methoxy>-2-methylpentanal; In tetrahydrofuran; at -78 - -20 ℃; for 2h; Further stages.;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: (2S,3R,4R,6R)-6-(2-Ethyl-[1,3]dithiolan-2-yl)-2,4-dimethyl-heptane-1,3,4-triol

: 149820-11-1
(2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide / 8 h / 0 °C

2.1: 98 percent / benzene / 12 h / Heating

3.1: 84 percent / calcium carbonate; mercury(II) perchlorate; water / tetrahydrofuran / 0.08 h

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

4.2: 83 percent / tetrahydrofuran / 2 h / -78 - -20 °C

With 1H-imidazole; mercury(II) perchlorate; water; calcium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: 944740-89-0
(2S,3R,4R,6R)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-7,7-ethylenedithio-2,4,6-trimethylnonane

: 149820-11-1
(2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 84 percent / calcium carbonate; mercury(II) perchlorate; water / tetrahydrofuran / 0.08 h

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

2.2: 83 percent / tetrahydrofuran / 2 h / -78 - -20 °C

With mercury(II) perchlorate; water; calcium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1016/j.tet.2007.02.044