(E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol

Base Information

Chemical Name:(E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol
CAS No.:1417560-01-0
Molecular Formula:C₂₉H₄₈O₃Si
Molecular Weight:472.784
Hs Code.:

Synonyms:(E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol

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Chemical Property of (E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol

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Technology Process of (E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol

There total 10 articles about (E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol 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: 92.0%

: 1417559-84-2
(E)-ethyl 4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-enoate

: 1417560-01-0
(E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 - -15 ℃; for 3h; Inert atmosphere;
DOI:10.1139/v2012-088

Reference yield:

: C₁₇H₃₆O₂Si

: 1417560-01-0
(E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / Inert atmosphere

2.1: triethylamine; hydrazine / ethanol; water / 68 °C / Reflux; Inert atmosphere

3.1: iodine; N,N,N',N'-tetramethylguanidine / tetrahydrofuran / 0.5 h / Inert atmosphere

4.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C / Inert atmosphere

4.2: 12 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.75 h / -78 - -10 °C / Inert atmosphere

6.1: dmap; pyridine / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere

7.1: lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride / dimethyl sulfoxide / 14 h / 50 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 - -15 °C / Inert atmosphere

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrapropylammonium perruthennate; iodine; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; copper(l) chloride; lithium chloride; hydrazine; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; 7.1: |Stille Cross Coupling;
DOI:10.1139/v2012-088

Reference yield:

: 138435-42-4
4-benzyloxybut-2-ynoic acid ethyl ester

: 1417560-01-0
(E)-4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: n-butyllithium; copper(l) cyanide / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere

2: lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride / dimethyl sulfoxide / 14 h / 50 °C / Inert atmosphere

3: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 - -15 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; copper(l) cyanide; diisobutylaluminium hydride; copper(l) chloride; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 2: |Stille Cross Coupling;
DOI:10.1139/v2012-088