(2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

Base Information

Chemical Name:(2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one
CAS No.:1447732-03-7
Molecular Formula:C₅₆H₁₀₆O₉Si₃
Molecular Weight:1007.71
Hs Code.:

(2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

Synonyms:(2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

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Chemical Property of (2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

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Technology Process of (2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

There total 5 articles about (2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-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: 35.0%

: 1447732-02-6
(2S,3R,4R,5S,6S,8E)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyl-2,4,6,8-tetramethyl-dec-8-en-1-al

: 1447731-98-7
C₃₀H₅₂O₆Si

: 1447732-04-8
(2S,3S,4R,5S,6S,8S,11R,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

: 1447732-03-7
(2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

Guidance literature:: C₃₀H₅₂O₆Si; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

(2S,3R,4R,5S,6S,8E)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxyl-2,4,6,8-tetramethyl-dec-8-en-1-al; In tetrahydrofuran; at -78 ℃; for 5h; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; Inert atmosphere;
DOI:10.1016/j.tet.2013.06.012

Reference yield:

: (3S,5S,6S,7R,9S)-3-(tert-butyldimethylsilyloxy)-6,8-dihydroxy-10-(4-methoxyphenyl)oxy-5,7,9-trimethyl-dec-1-yne

: 1447732-03-7
(2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate; mercury(II) diacetate / tetrahydrofuran / 8 h / 45 °C / pH 7 / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 5 h / -78 °C / Inert atmosphere

3.3: Inert atmosphere

With mercury(II) diacetate; pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2013.06.012

Reference yield:

: 1447731-97-6
C₃₀H₅₀O₅Si

: 1447732-03-7
(2S,3S,4R,5S,6S,8S,11S,12R,13S,14R,15S,16S,18E)-1-(8,15-bis(tert-butyldimethylsilyloxy)-13-triethylsilyloxy-11-methoxy-4-methoxybenzyl)oxy-2,4,6,12,14,16,18-heptamethyl-3,5-[(dimethyl-methylene)dioxy]-icos-18-en-9-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridinium p-toluenesulfonate; mercury(II) diacetate / tetrahydrofuran / 8 h / 45 °C / pH 7 / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 5 h / -78 °C / Inert atmosphere

2.3: Inert atmosphere

With mercury(II) diacetate; pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1016/j.tet.2013.06.012