(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

Base Information

Chemical Name:(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate
CAS No.:1269803-20-4
Molecular Formula:C₄₀H₆₀O₆
Molecular Weight:636.913
Hs Code.:

Synonyms:(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

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Chemical Property of (S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

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Technology Process of (S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

There total 59 articles about (S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate 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: 85.0%

: 1269803-12-4
(4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-ol

: 1269803-11-3
(S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexanoic acid

: 1269803-20-4
(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

Guidance literature:: (S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexanoic acid; With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In toluene; at 20 ℃; for 6h; Inert atmosphere;

(4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-ol; With dmap; In toluene; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1002/ejoc.201001205

Reference yield:

: 1269803-28-2
(S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexan-1-ol

: 1269803-20-4
(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / Inert atmosphere

2.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / toluene / 6 h / 20 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; toluene; 2.1: Yamaguchi esterification / 2.2: Yamaguchi esterification;
DOI:10.1002/ejoc.201001205

Reference yield:

: 1146690-87-0
(3S)-9-(benzyloxy)-3-(2-bromo-1-ethoxyethoxy)-1-nonyne

: 1269803-20-4
(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

Guidance literature:: Multi-step reaction with 17 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 0.5 h / Inert atmosphere; Reflux

2.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

3.1: Jones reagent / acetone / 0 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere

5.1: iodine / dichloromethane / -78 - 20 °C / Inert atmosphere

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / Inert atmosphere

7.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

7.2: 3 h / -20 - 0 °C / Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

8.2: 3 h / -78 °C / Inert atmosphere

9.1: lithium borohydride; water / diethyl ether / 0 °C

10.1: 1H-imidazole / dichloromethane / 3.17 h / 0 - 20 °C / Inert atmosphere

11.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C

12.1: sodium periodate / tetrahydrofuran; water / 1 h / 23 °C

13.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere

14.1: sodium hydride / tetrahydrofuran / 1.17 h / 0 - 20 °C / Inert atmosphere

14.2: 0 - 20 °C / Inert atmosphere

15.1: pyridine hydrofluoride / tetrahydrofuran / 20 °C

16.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / Inert atmosphere

17.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / toluene / 6 h / 20 °C / Inert atmosphere

17.2: 3 h / 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; Jones reagent; lithium borohydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; nickel(II) chloride hexahydrate; 2,2'-azobis(isobutyronitrile); pyridine hydrofluoride; [bis(acetoxy)iodo]benzene; 2,4,6-trichlorobenzoyl chloride; water; iodine; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; pivaloyl chloride; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; acetonitrile; benzene; 3.1: Jones oxidation / 17.1: Yamaguchi esterification / 17.2: Yamaguchi esterification;
DOI:10.1002/ejoc.201001205