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

Base Information

Chemical Name:(E)-ethyl 4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-enoate
CAS No.:1417559-84-2
Molecular Formula:C₃₁H₅₀O₄Si
Molecular Weight:514.821
Hs Code.:

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

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

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

There total 8 articles about (E)-ethyl 4-(benzyloxy)-3-(((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)but-2-enoate 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: 85.0%

: 1417559-81-9,1417559-82-0
(Z)-ethyl 4-(benzyloxy)-3-(tributylstannyl)but-2-enoate

: 1417559-83-1
((4R,5R)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl acetate

: 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

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride; lithium chloride; In dimethyl sulfoxide; at 50 ℃; for 14h; stereoselective reaction; Inert atmosphere;
DOI:10.1139/v2012-088

Reference yield:

: C₁₇H₃₆O₂Si

: 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

Guidance literature:: Multi-step reaction with 7 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

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

: 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

Guidance literature:: Multi-step reaction with 2 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

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