(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-1-yn-3-ol

Base Information

Chemical Name:(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-1-yn-3-ol
CAS No.:1332623-03-6
Molecular Formula:C₂₆H₃₄O₄Si
Molecular Weight:438.639
Hs Code.:

Synonyms:(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-1-yn-3-ol

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Chemical Property of (3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-1-yn-3-ol

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Technology Process of (3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-1-yn-3-ol

There total 5 articles about (3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-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:

: C₂₄H₃₂O₄Si

: 1066-54-2
trimethylsilylacetylene

: 1332623-03-6
(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-1-yn-3-ol

Guidance literature:: trimethylsilylacetylene; With ethylmagnesium bromide; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;

C₂₄H₃₂O₄Si; In tetrahydrofuran; at -78 - 0 ℃; for 16h; diastereoselective reaction; Further stages; Inert atmosphere;
DOI:10.1021/ol202116k

Reference yield:

: 1301166-50-6
(4R)-4-[(1S)-1-methoxymethoxy-3-buten-1-yl]-2,2-dimethyl-1,3-dioxolane

: 1332623-03-6
(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-1-yn-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: water; pyridinium p-toluenesulfonate / ethanol / 5 h / 20 - 60 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

4.1: ethylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 16 h / -78 - 0 °C / Inert atmosphere

With 1H-imidazole; ethylmagnesium bromide; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 4.2: Grignard reaction;
DOI:10.1021/ol202116k

Reference yield:

: 1332623-01-4
(2R,3S)-3-(methoxymethoxy)hex-5-ene-1,2-diol

: 1332623-03-6
(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-methoxymethoxy-6-hepten-1-yn-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

3.1: ethylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 16 h / -78 - 0 °C / Inert atmosphere

With 1H-imidazole; ethylmagnesium bromide; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.2: Grignard reaction;
DOI:10.1021/ol202116k