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

Base Information

Chemical Name:(R)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate
CAS No.:1422039-49-3
Molecular Formula:C₃₃H₄₄O₅
Molecular Weight:520.709
Hs Code.:

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

There total 8 articles about (R)-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%

: 1422039-47-1
(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

: 1422039-49-3
(R)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-ynyl benzoate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h; Cooling with ice;
DOI:10.1016/j.tet.2012.12.045

Reference yield:

: 38145-93-6
1,2:3,4-di-O-isopropylidene-D-mannitol

: 1422039-49-3
(R)-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 8 steps

1.1: sodium periodate / dichloromethane; water / 4 h / 0 - 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 0 °C

2.2: 0.5 h / 0 °C

3.1: hydrogen / ethanol / 0.5 h / 1034.32 Torr

4.1: toluene-4-sulfonic acid / methanol / 20 h / 0 °C

5.1: di(n-butyl)tin oxide; dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Cooling with ice

5.2: 4 h / 0 - 20 °C

6.1: potassium carbonate / methanol / 1 h / 0 °C / Inert atmosphere

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

8.1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Cooling with ice

With dmap; sodium periodate; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination;
DOI:10.1016/j.tet.2012.12.045

Reference yield:

: 1422039-43-7
(4S,4'R,5R)-5-((Z)-5-(benzyloxy)pent-1-enyl)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolane)

: 1422039-49-3
(R)-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 6 steps

1.1: hydrogen / ethanol / 0.5 h / 1034.32 Torr

2.1: toluene-4-sulfonic acid / methanol / 20 h / 0 °C

3.1: di(n-butyl)tin oxide; dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Cooling with ice

3.2: 4 h / 0 - 20 °C

4.1: potassium carbonate / methanol / 1 h / 0 °C / Inert atmosphere

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

6.1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Cooling with ice

With dmap; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1016/j.tet.2012.12.045