((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol

Base Information

Chemical Name:((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol
CAS No.:871095-05-5
Molecular Formula:C₂₈H₄₆O₄Si
Molecular Weight:474.756
Hs Code.:

Synonyms:((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol

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Chemical Property of ((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol

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Technology Process of ((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol

There total 12 articles about ((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol 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:

: 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

: 871095-05-5
((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol

Guidance literature:: With diethylaluminium chloride; In dichloromethane; toluene; at -50 ℃; for 3h;
DOI:10.1021/ol0515762

Reference yield:

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

: 871095-05-5
((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: LiCl / Pd(PPh₃)4 / diethyl ether

2.1: Et₂AlCl / CH₂Cl₂; toluene / 3 h / -50 °C

With 1,1-Dibromoethane; diethylaluminium chloride; magnesium; In diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol0515762

Reference yield:

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

: 871095-05-5
((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol

Guidance literature:: Multi-step reaction with 4 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

4.1: Et₂AlCl / CH₂Cl₂; toluene / 3 h / -50 °C

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