(R)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

Base Information

Chemical Name:(R)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate
CAS No.:1402698-57-0
Molecular Formula:C₂₁H₂₄O₃Si
Molecular Weight:352.505
Hs Code.:

Synonyms:

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Chemical Property of (R)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

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Technology Process of (R)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

There total 3 articles about (R)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate 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:

: 1402698-41-2
(3-chloroprop-1-ynyl)dimethyl(o-tolyl)silane

: 6908-41-4,58590-49-1
4-(methoxycarbonyl)benzyl alcohol

: (S)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

: 1402698-57-0
(R)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

Guidance literature:: With hex-3-yne; [Ir(1,5-cyclooctadiene)₂]triflate; sodium carbonate; isopropyl alcohol; (R)-segphos; In tetrahydrofuran; at 90 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Sealed tube;
DOI:10.1002/anie.201203334

Reference yield:

: 1402698-41-2
(3-chloroprop-1-ynyl)dimethyl(o-tolyl)silane

: 1571-08-0
methyl 4-formylbenzoate

: (S)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

: 1402698-57-0
(R)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

Guidance literature:: With hex-3-yne; [Ir(1,5-cyclooctadiene)₂]triflate; sodium carbonate; isopropyl alcohol; (R)-segphos; In tetrahydrofuran; at 90 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Sealed tube;
DOI:10.1002/anie.201203334

Reference yield:

: 17146-06-4
dimethyl(o-tolyl)chlorosilane

: (S)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

: 1402698-57-0
(R)-methyl 4-(4-(dimethyl(o-tolyl)silyl)-1-hydroxybut-3-ynyl)benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 2 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: [Ir(1,5-cyclooctadiene)₂]triflate; hex-3-yne; sodium carbonate; isopropyl alcohol; (R)-segphos / tetrahydrofuran / 20 h / 90 °C / Inert atmosphere; Sealed tube

With n-butyllithium; hex-3-yne; [Ir(1,5-cyclooctadiene)₂]triflate; sodium carbonate; isopropyl alcohol; (R)-segphos; In tetrahydrofuran; hexane; toluene;
DOI:10.1002/anie.201203334