(3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

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Chemical Name:(3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one
CAS No.:1449307-07-6
Molecular Formula:C₂₅H₄₆O₆Si
Molecular Weight:470.722
Hs Code.:

(3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

Synonyms:(3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

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Chemical Property of (3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

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Technology Process of (3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

There total 5 articles about (3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-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: 87.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 1449306-99-3
(3S,4R,5R)-3-[(R)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

: 1449307-07-6
(3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere;
DOI:10.1016/j.tet.2013.05.091

Reference yield:

: 1449307-34-9
C₁₄H₂₄O₅

: 1449307-07-6
(3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: boron trifluoride diethyl etherate / ethyl acetate / 8 h / 0 - 20 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: trimethyl(benzyl)ammonium fluoride / tetrahydrofuran / 2.3 h / -78 - -10 °C / Molecular sieve; Inert atmosphere

4.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; trimethyl(benzyl)ammonium fluoride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1016/j.tet.2013.05.091

Reference yield:

: 1449307-33-8
C₁₇H₂₈O₅

: 1449307-07-6
(3R,4R,5R)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: trimethyl(benzyl)ammonium fluoride / tetrahydrofuran / 2.3 h / -78 - -10 °C / Molecular sieve; Inert atmosphere

3.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

With trimethyl(benzyl)ammonium fluoride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2013.05.091