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

Base Information

Chemical Name:(R)-2-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylsulfonyloxy)ethyl benzoate
CAS No.:1422039-45-9
Molecular Formula:C₂₇H₃₆O₈S
Molecular Weight:520.644
Hs Code.:

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

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

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

There total 6 articles about (R)-2-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylsulfonyloxy)ethyl 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: 90.0%

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

: 124-63-0
methanesulfonyl chloride

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

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 4h; 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

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

Guidance literature:: Multi-step reaction with 6 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 / 0 °C

5.2: 8 h / 0 - 20 °C

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

With dmap; sodium periodate; potassium tert-butylate; hydrogen; di(n-butyl)tin oxide; 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:

: 13039-93-5
2,2:4,5-di-O-isopropylidene-D-arabinose

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

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 0.5 h / 0 °C

2.1: hydrogen / ethanol / 0.5 h / 1034.32 Torr

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

4.1: di(n-butyl)tin oxide; dmap; triethylamine / dichloromethane / 0.5 h / 0 °C

4.2: 8 h / 0 - 20 °C

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

With dmap; potassium tert-butylate; hydrogen; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;
DOI:10.1016/j.tet.2012.12.045