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

Base Information

Chemical Name:(6S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-ol
CAS No.:1431879-85-4
Molecular Formula:C₂₂H₃₄O₅Si
Molecular Weight:406.594
Hs Code.:

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

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

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

There total 3 articles about (6S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-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: 87.0%

: 1431879-70-7
(4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal

: 1066-54-2
trimethylsilylacetylene

: 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

Guidance literature:: trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

(4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal; In tetrahydrofuran; at -78 ℃; for 1h; 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

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

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 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

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

Guidance literature:: Multi-step reaction with 3 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

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