(S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate

Base Information

Chemical Name:(S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate
CAS No.:1422039-50-6
Molecular Formula:C₃₃H₄₄O₅
Molecular Weight:520.709
Hs Code.:

Synonyms:(S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate

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Chemical Property of (S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate

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Technology Process of (S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate

There total 9 articles about (S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate 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: 89.0%

: 1422039-48-2
(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol

: 98-88-4
benzoyl chloride

: 1422039-50-6
(S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate

Guidance literature:: (R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol; With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.25h;

benzoyl chloride; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/j.tet.2012.12.045

Reference yield:

: 1422039-45-9
(R)-2-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylsulfonyloxy)ethyl benzoate

: 1422039-50-6
(S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran / 4 h / 20 °C

2.1: n-butyllithium; boron trifluoride diethyl etherate / tetrahydrofuran / 0.75 h / -78 °C

3.1: dmap; triethylamine / dichloromethane / 0.25 h / 0 °C

3.2: 2 h / 0 °C

With dmap; n-butyllithium; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tet.2012.12.045

Reference yield:

: 1422039-44-8
(R)-2-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl benzoate

: 1422039-50-6
(S)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice

2.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran / 4 h / 20 °C

3.1: n-butyllithium; boron trifluoride diethyl etherate / tetrahydrofuran / 0.75 h / -78 °C

4.1: dmap; triethylamine / dichloromethane / 0.25 h / 0 °C

4.2: 2 h / 0 °C

With dmap; n-butyllithium; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tet.2012.12.045