(2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-ol

Base Information

Chemical Name:(2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-ol
CAS No.:1609186-64-2
Molecular Formula:C₂₁H₂₈O₅
Molecular Weight:360.45
Hs Code.:

Synonyms:(2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-ol

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Chemical Property of (2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-ol

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Technology Process of (2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-ol

There total 5 articles about (2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-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%

: 1609186-60-8
(3aR,5S,6aR)-5-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxole

: 16088-62-3
(S)-Propylene oxide

: 1609186-64-2
(2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-ol

Guidance literature:: With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃;
DOI:10.1016/j.tet.2014.04.026

Reference yield:

: 1609186-58-4
(S)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-4-(trimethylsilyl)but-3-yn-1-ol

: 1609186-64-2
(2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C

1.2: 2 h / 20 °C

2.1: boron trifluoride diethyl etherate; n-butyllithium / tetrahydrofuran; hexane / -78 °C

With n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; hexane; mineral oil;
DOI:10.1016/j.tet.2014.04.026

Reference yield:

: 20720-51-8
(3aR,5S,6aR)-2,2-dimethyl-5-[(2S)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

: 1609186-64-2
(2R,7S)-7-(benzyloxy)-7-((3aR,5S,6aR)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)hept-4-yn-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: boron trifluoride diethyl etherate; n-butyllithium / tetrahydrofuran; hexane / -78 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C

2.2: 2 h / 20 °C

3.1: boron trifluoride diethyl etherate; n-butyllithium / tetrahydrofuran; hexane / -78 °C

With n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; hexane; mineral oil;
DOI:10.1016/j.tet.2014.04.026