(2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

Base Information

Chemical Name:(2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol
CAS No.:1332623-05-8
Molecular Formula:C₂₃H₂₈O₄Si
Molecular Weight:396.558
Hs Code.:

Synonyms:(2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

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Chemical Property of (2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

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Technology Process of (2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

There total 7 articles about (2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol 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:

: 1332623-04-7
(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-6-hepten-1-yne-3,4-diol

: 1332623-05-8
(2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

: 1400814-17-6
(2R,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

Guidance literature:: (3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-6-hepten-1-yne-3,4-diol; With ozone; In methanol; dichloromethane; at -78 ℃; for 0.416667h;

With dimethylsulfide; sodium hydrogencarbonate; In methanol; dichloromethane; at -78 - 20 ℃; optical yield given as %de;
DOI:10.1021/ol202116k

Reference yield:

: 1332623-02-5
(2R,3S)-1-(tert-butyldiphenylsilyloxy)-3-methoxymethoxy-5-hexen-2-ol

: 1332623-05-8
(2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

: 1400814-17-6
(2R,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

Guidance literature:: Multi-step reaction with 4 steps

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

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

2.2: 16 h / -78 - 0 °C / Inert atmosphere

3.1: zinc dibromide / dichloromethane / 0.5 h / 20 °C

4.1: ozone / methanol; dichloromethane / 0.42 h / -78 °C

4.2: -78 - 20 °C

With ethylmagnesium bromide; sodium hydrogencarbonate; Dess-Martin periodane; ozone; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane; 2.2: Grignard reaction;
DOI:10.1021/ol202116k

Reference yield:

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

: 1332623-05-8
(2S,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

: 1400814-17-6
(2R,4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-5-ethynyltetrahydrofuran-2,4-diol

Guidance literature:: Multi-step reaction with 6 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

5.1: zinc dibromide / dichloromethane / 0.5 h / 20 °C

6.1: ozone / methanol; dichloromethane / 0.42 h / -78 °C

6.2: -78 - 20 °C

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