allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate

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Chemical Name:allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate
CAS No.:1120309-24-1
Molecular Formula:C₃₇H₅₁NO₈Si
Molecular Weight:665.899
Hs Code.:

Synonyms:allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate

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Chemical Property of allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate

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Technology Process of allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate

There total 22 articles about allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate 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:

: C₃₃H₄₇NO₆Si

: 2937-50-0
Allyl chloroformate

: 1120309-24-1
allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate

Guidance literature:: With pyridine; In tetrahydrofuran; water; at 20 ℃; for 0.333333h;
DOI:10.1016/j.tet.2010.05.050

Reference yield:

: 1120308-99-7
(R)-1-(allyloxy)hex-3-yn-2-ol

: 1120309-24-1
allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate

Guidance literature:: Multi-step reaction with 13 steps

1.1: copper(I) bromide; lithium bromide; zinc / tetrahydrofuran; ethylene dibromide; isopropyl alcohol / 18 h / 20 °C / Reflux

2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

5.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / -20 - 0 °C

5.2: 1.5 h / -20 °C

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether; toluene / 6 h / 0 °C

7.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 °C

7.2: 2 h / -78 °C

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / Reflux

9.1: water; toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C

10.1: pyridine; dmap / dichloromethane / 14 h / 20 °C

11.1: sodium azide / N,N-dimethyl-formamide / 72 h / 20 °C

12.1: water; triphenylphosphine / tetrachloromethane / 22 h / 20 °C

13.1: pyridine / tetrahydrofuran; water / 0.33 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; n-butyllithium; sodium azide; potassium tert-butylate; tetrabutyl ammonium fluoride; water; isopropylmagnesium chloride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; copper(I) bromide; lithium bromide; zinc; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; ethylene dibromide; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 3.1: [2,3]-Wittig rearrangement / 12.1: Staudinger reaction;
DOI:10.1021/ol8029142

Reference yield:

: 1120308-97-5
1-(allyloxy)hex-3-yn-2-one

: 1120309-24-1
allyl {(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-[(E)-2-((1S,2S)-2-ethyl-5-oxocyclohex-3-enyl)vinyl]-3-hydroxy-4-methoxymethoxyhex-1-yl}carbamate

Guidance literature:: Multi-step reaction with 14 steps

1.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); isopropyl alcohol / 0.75 h / 20 °C

2.1: copper(I) bromide; lithium bromide; zinc / tetrahydrofuran; ethylene dibromide; isopropyl alcohol / 18 h / 20 °C / Reflux

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

6.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / -20 - 0 °C

6.2: 1.5 h / -20 °C

7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether; toluene / 6 h / 0 °C

8.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 °C

8.2: 2 h / -78 °C

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / Reflux

10.1: water; toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C

11.1: pyridine; dmap / dichloromethane / 14 h / 20 °C

12.1: sodium azide / N,N-dimethyl-formamide / 72 h / 20 °C

13.1: water; triphenylphosphine / tetrachloromethane / 22 h / 20 °C

14.1: pyridine / tetrahydrofuran; water / 0.33 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; sodium azide; potassium tert-butylate; tetrabutyl ammonium fluoride; water; isopropylmagnesium chloride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; isopropyl alcohol; copper(I) bromide; lithium bromide; zinc; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; ethylene dibromide; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 4.1: [2,3]-Wittig rearrangement / 13.1: Staudinger reaction;
DOI:10.1021/ol8029142