(S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one

Base Information

Chemical Name:(S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one
CAS No.:1431879-71-8
Molecular Formula:C₂₂H₃₂O₅Si
Molecular Weight:404.579
Hs Code.:

Synonyms:(S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one

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Chemical Property of (S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one

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Technology Process of (S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one

There total 4 articles about (S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one 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: 83.0%

: 1431879-85-4
(6S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-ol

: 1431879-71-8
(S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one

Guidance literature:: With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol400487e

Reference yield:

: 1431879-69-4
(4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol

: 1431879-71-8
(S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -60 °C / Inert atmosphere

1.2: 0.33 h / -60 - 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1021/ol400487e

Reference yield:

: (R)-4-((S)-1-((4-methoxybenzyl)oxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane

: 1431879-71-8
(S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -60 °C / Inert atmosphere

2.2: 0.33 h / -60 - 0 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; borane; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1021/ol400487e