3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol

Base Information

Chemical Name:3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol
CAS No.:540727-82-0
Molecular Formula:C₃₄H₅₄O₇SSi
Molecular Weight:634.95
Hs Code.:

Synonyms:3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol

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Chemical Property of 3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol

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Technology Process of 3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol

There total 10 articles about 3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-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: 95.0%

: 121942-44-7
(3-Benzenesulfonyl-propoxy)-tert-butyl-dimethyl-silane

: 290334-86-0
4-(1-benzyloxypentyl)-2,2-dimethyl-5-oxiranyl[1,3]dioxolane

: 540727-82-0
3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol

Guidance literature:: (3-Benzenesulfonyl-propoxy)-tert-butyl-dimethyl-silane; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

With copper(l) iodide; In tetrahydrofuran; hexane; at -80 ℃; for 1h;

4-(1-benzyloxypentyl)-2,2-dimethyl-5-oxiranyl[1,3]dioxolane; In tetrahydrofuran; hexane; at -80 - -20 ℃; for 12h;
DOI:10.1021/jo0269058

Reference yield:

: 85325-93-5,105454-09-9,105454-10-2
1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol

: 540727-82-0
3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: CuCN / tetrahydrofuran / 0.5 h / -80 °C

1.2: 98 percent / tetrahydrofuran / 8 h / -80 °C

2.1: 95 percent / sodium hydride / tetrahydrofuran / 12 h / 20 °C

3.1: 2.01 g / CuCl₂*2H₂O / acetonitrile / 0.67 h / 0 °C

4.1: pyridine / CH₂Cl₂ / 24 h / 0 °C

5.1: 1 percent / K₂CO₃ / methanol / 1 h / 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

6.2: CuI / tetrahydrofuran; hexane / 1 h / -80 °C

6.3: 95 percent / tetrahydrofuran; hexane / 12 h / -80 - -20 °C

With pyridine; n-butyllithium; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo0269058

Reference yield:

: 3969-59-3
mannitol triacetonide

: 540727-82-0
3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 8.5 g / concentrated HCl / aq. ethanol / 1 h / 45 °C

2.1: 83 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / -80 - -20 °C

3.1: triethylamine / CH₂Cl₂ / 10 h / -80 - -20 °C

4.1: 3.8 g / K₂CO₃ / methanol / 2 h / 20 °C

5.1: CuCN / tetrahydrofuran / 0.5 h / -80 °C

5.2: 98 percent / tetrahydrofuran / 8 h / -80 °C

6.1: 95 percent / sodium hydride / tetrahydrofuran / 12 h / 20 °C

7.1: 2.01 g / CuCl₂*2H₂O / acetonitrile / 0.67 h / 0 °C

8.1: pyridine / CH₂Cl₂ / 24 h / 0 °C

9.1: 1 percent / K₂CO₃ / methanol / 1 h / 0 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

10.2: CuI / tetrahydrofuran; hexane / 1 h / -80 °C

10.3: 95 percent / tetrahydrofuran; hexane / 12 h / -80 - -20 °C

With pyridine; hydrogenchloride; dmap; n-butyllithium; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo0269058