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

Base Information

Chemical Name:(3aR,5S,6aR)-5-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:1609186-60-8
Molecular Formula:C₁₈H₂₂O₄
Molecular Weight:302.37
Hs Code.:

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

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Chemical Property of (3aR,5S,6aR)-5-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxole

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Technology Process of (3aR,5S,6aR)-5-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxole

There total 4 articles about (3aR,5S,6aR)-5-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl tetrahydrofuro[2,3-d][1,3]dioxole 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: 70.0%

: 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

: 100-39-0
benzyl bromide

: 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

Guidance literature:: (S)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-4-(trimethylsilyl)but-3-yn-1-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.333333h;

benzyl bromide; In tetrahydrofuran; mineral oil; at 20 ℃; for 2h;
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

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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

: 1609186-71-1
C₁₆H₃₂O₇SSi

: 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

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

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

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

3.2: 2 h / 20 °C

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