methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate

Base Information

Chemical Name:methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate
CAS No.:185903-43-9
Molecular Formula:C₂₆H₃₄O₅Si
Molecular Weight:454.638
Hs Code.:

Synonyms:methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate

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Chemical Property of methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate

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Technology Process of methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate

There total 6 articles about methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate 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: 86.0%

: 5927-18-4
trimethyl phosphonoacetate

: 157406-33-2
5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal

: 185903-43-9
methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile;
DOI:10.1016/S0040-4039(00)77047-X

Reference yield:

: 26260-02-6
2-iodobenzaldehyde

: 185903-43-9
methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, hexanes, -20 deg C, 30 min, 2.) THF, room temperature, overnight

2: 82 percent / Et₃N / CH₂Cl₂ / 7 h / Ambient temperature

3: 32 percent / Pd(PPh₃)2Cl₂, Et₃N, CuI / tetrahydrofuran / 48 h / Ambient temperature

4: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

5: 1.) LiCl, DBU / 1.) MeCN, room temperatrure, 2.) MeCN, room temperature

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961049j

Reference yield:

: 5159-41-1
2-iodobenzyl alcohol

: 185903-43-9
methyl 7-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>hept-2-en-6-ynoate

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / pyridinium chloroformate / CH₂Cl₂ / Ambient temperature

2: 1.) n-BuLi / 1.) THF, hexanes, -20 deg C, 30 min, 2.) THF, room temperature, overnight

3: 82 percent / Et₃N / CH₂Cl₂ / 7 h / Ambient temperature

4: 32 percent / Pd(PPh₃)2Cl₂, Et₃N, CuI / tetrahydrofuran / 48 h / Ambient temperature

5: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

6: 1.) LiCl, DBU / 1.) MeCN, room temperatrure, 2.) MeCN, room temperature

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; pyridinium chloroformate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961049j