(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

Base Information

Chemical Name:(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one
CAS No.:1132970-14-9
Molecular Formula:C₄₄H₆₄O₇Si
Molecular Weight:733.073
Hs Code.:

(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

Synonyms:(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

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Chemical Property of (3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

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Technology Process of (3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

There total 31 articles about (3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-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: 60.0%

: 1132969-98-2
methyl (2Z,4E,6R,7S,8S,10E,12E,14S,15R,16S,17R,18S,19S)-19-(tert-butyldiphenylsilyloxy)-7,15,17-trihydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethylicosa-2,4,10,12-tetraenoate

: 1132970-14-9
(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

Guidance literature:: methyl (2Z,4E,6R,7S,8S,10E,12E,14S,15R,16S,17R,18S,19S)-19-(tert-butyldiphenylsilyloxy)-7,15,17-trihydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethylicosa-2,4,10,12-tetraenoate; With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 12h;

With N-ethyl-N,N-diisopropylamine; In toluene; Further stages; Inert atmosphere;
DOI:10.1002/chem.201102797

Reference yield:

: C₅₁H₆₇Cl₃O₉Si

: 1132970-14-9
(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

Guidance literature:: With dmap; In toluene; at 20 - 40 ℃; for 5h; regioselective reaction; Inert atmosphere;
DOI:10.1002/anie.200804645

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1132970-14-9
(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

Guidance literature:: Multi-step reaction with 19 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 44 h / 20 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

3.2: 0.42 h / 0 °C

4.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

5.1: dichloromethane / -78 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

7.1: pyridine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere

8.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C

9.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 118 h / -10 - -5 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid / 0.33 h / 20 °C / Inert atmosphere

11.1: lithium hydroxide / tetrahydrofuran; methanol; water / 0.42 h / 20 °C

12.1: sodium periodate / chloroform / 0.47 h / 20 °C / Inert atmosphere

13.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / toluene / 35 h / 20 °C / Inert atmosphere

13.2: 17 h / 20 °C / Inert atmosphere

14.1: tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; Triethoxysilane / dichloromethane / 0 - 20 °C / Inert atmosphere

14.2: 0 - 20 °C / Inert atmosphere

15.1: tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

16.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

17.1: dmap / dichloromethane / 20 °C / Inert atmosphere

17.2: 0.25 h / 20 °C / Inert atmosphere

18.1: CSA / methanol / 20 °C / Inert atmosphere

18.2: Inert atmosphere

19.1: lithium hydroxide / tetrahydrofuran; methanol; water / 12 h / 20 °C

19.2: Inert atmosphere

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; lithium borohydride; Triethoxysilane; tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; (-)-N-methylephedrine; hydroxylamine hydrochloride; hydrogen; boric acid; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; potassium bromide; lithium hydroxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/chem.201102797