tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

Base Information

Chemical Name:tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane
CAS No.:871094-98-3
Molecular Formula:C₄₇H₆₀O₄Si
Molecular Weight:717.077
Hs Code.:

Synonyms:tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

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Chemical Property of tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

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Technology Process of tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

There total 11 articles about tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane 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:

: 286440-95-7
1-[(5-bromopentyloxy)methyl]-4-methoxybenzene

: 871094-95-0
(3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate

: 871094-98-3
tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

Guidance literature:: 1-[(5-bromopentyloxy)methyl]-4-methoxybenzene; With 1,1-Dibromoethane; magnesium; In diethyl ether; at 10 ℃; for 4h;

(3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate; With lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethyl ether; at 20 ℃; for 0.5h;
DOI:10.1021/ol0515762

Reference yield:

: 286440-95-7
1-[(5-bromopentyloxy)methyl]-4-methoxybenzene

: 871094-95-0
(3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate

: tert-Butyl-dimethyl-((2R,3S,3aS,6aR)-3-trityloxymethyl-1,2,3,3a,4,6a-hexahydro-pentalen-2-yloxy)-silane

: 871094-98-3
tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

Guidance literature:: 1-[(5-bromopentyloxy)methyl]-4-methoxybenzene; With 1,1-Dibromoethane; magnesium; In diethyl ether; at 10 ℃; for 4h;

(3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate; With lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether;
DOI:10.1021/ol0515762

Reference yield:

: 871095-04-4
(3aS,4S,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)hexahydropentalen-2(1H)-one

: 871094-98-3
tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 5 h / -108 °C

2.2: tetrahydrofuran; toluene / -108 - 20 °C

3.1: Mg; dibromoethane / diethyl ether / 4 h / 10 °C

3.2: LiCl / Pd(PPh₃)4 / diethyl ether

With dmap; 1,1-Dibromoethane; potassium hexamethylsilazane; magnesium; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol0515762