(2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

Base Information

Chemical Name:(2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one
CAS No.:1356354-23-8
Molecular Formula:C₄₆H₈₄O₆Si₂
Molecular Weight:789.34
Hs Code.:

(2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

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Chemical Property of (2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

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Technology Process of (2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

There total 4 articles about (2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-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:

: 1356109-14-2
O-((1R,2S,3S,4E,6S)-3-{[tert-butyl(dimethyl)silyl]-oxy}-1-{(1R,4S,5S,6S)-6-{[tert-butyl(dimethyl)silyl]-oxy}-4-methoxy-8-[(4-methoxybenzyl)oxy]-1,3,3,5-tetramethyl-2-oxooctyl}-2,4,6,8-tetramethylnona-4,7-dienyl) S-methyl dithiocarbonate

: 1356354-23-8
(2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

: 1356108-69-4
(5S,6S,7S,10R,12S,13S)-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disilaheptadecan-9-one

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201101129

Reference yield:

: 1356108-66-1
(5S,6S,7S,10R,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5 trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disilaheptadecan-9-one

: 1356354-23-8
(2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 6 h / -78 - 0 °C

2.1: triethyl borane; tri-n-butyl-tin hydride / hexane; toluene / 1 h / 20 °C / Inert atmosphere

With triethyl borane; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; toluene; 2.1: Barton-McCombie deoxygenation;
DOI:10.1002/ejoc.201101129

Reference yield:

: 1268687-74-6
(5S,6S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

: 1356354-23-8
(2R,5S,6S,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2-{(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1R)-1,3-dimethylbut-2-enyl]-2,4-dimethylcyclopentyl}-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: titanium tetrachloride; triethylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 3.5 h / -78 - 0 °C / Inert atmosphere

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

2.2: 6 h / -78 - 0 °C

3.1: triethyl borane; tri-n-butyl-tin hydride / hexane; toluene / 1 h / 20 °C / Inert atmosphere

With triethyl borane; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; titanium tetrachloride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Mukaiyama reaction / 1.2: Mukaiyama reaction / 3.1: Barton-McCombie deoxygenation;
DOI:10.1002/ejoc.201101129