(2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne

Base Information

Chemical Name:(2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne
CAS No.:1359717-96-6
Molecular Formula:C₂₈H₂₆F₂O₄Se
Molecular Weight:543.469
Hs Code.:

Synonyms:(2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne

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Chemical Property of (2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne

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Technology Process of (2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne

There total 7 articles about (2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne 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: 82.0%

: 1359717-93-3
(2R,3R,4R)-3,4-bis(O-benzyl)-1,1-difluoro-1-(phenylselanyl)-hex-5-yn-2,3,4-triol

: 108-24-7
acetic anhydride

: 1359717-96-6
(2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.jfluchem.2011.02.015

Reference yield:

: 171863-59-5
(((2R,3R)-2,3-bis(benzyloxy)pent-4-yn-1-yl)oxy)(tert-butyl)dimethylsilane

: 1359717-96-6
(2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 1 h / -60 °C / Molecular sieve; Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.1: Dess-Martin oxidation;
DOI:10.1016/j.jfluchem.2011.02.015

Reference yield:

: 162630-99-1
(2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal

: 1359717-96-6
(2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / methanol / 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.1: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 1 h / -60 °C / Molecular sieve; Inert atmosphere

4.2: 1 h / 20 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; triethylamine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Dess-Martin oxidation;
DOI:10.1016/j.jfluchem.2011.02.015