7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

Base Information

Chemical Name:7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol
CAS No.:756523-94-1
Molecular Formula:C₂₁H₃₄O₄Si
Molecular Weight:378.584
Hs Code.:

7-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

Synonyms:7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

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Chemical Property of 7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

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Technology Process of 7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

There total 1 articles about 7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-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:

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: 142860-84-2
4-(p-methoxybenzyloxy)-1,2-epoxybutane

: 756523-94-1
7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

Guidance literature:: tert-Butyldimethyl(prop-2-ynyloxy)silane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

4-(p-methoxybenzyloxy)-1,2-epoxybutane; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 - 25 ℃;
DOI:10.1002/anie.200460042

Reference yield:

: 756523-94-1
7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

: 2-Hydroxy-6-((1E,3Z)-penta-1,3-dienyl)-benzoic acid (S)-1-[(2R,3S)-((Z)-3-hepta-1,6-dienyl)-oxiranylmethyl]-3-(4-methoxy-benzyloxy)-propyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyridine; dmap / dichloromethane / 12 h / 20 °C

2.1: acetic acid / tetrahydrofuran / 2 h / 60 °C

3.1: hydrogen; triethylamine / Lindlar's catalyst / tetrahydrofuran / 8 h / 760 Torr

4.1: titanium(IV) isopropylate; DIPT / dichloromethane / 0.5 h / -20 °C

4.2: tert-butyl hydroperoxide / 15; 23 / 16 h / -20 °C

5.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran

6.2: 13 / -10 °C

7.1: potassium carbonate / methanol / 12 h / 20 °C

8.1: sodium hexamethyldisilazane / tetrahydrofuran

8.2: 13 / 0 - 25 °C

With pyridine; titanium(IV) isopropylate; dmap; DIPT; hydrogen; sodium hexamethyldisilazane; potassium carbonate; Dess-Martin periodane; acetic acid; triethylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; 3.1: Lindlar hydrogenation / 4.1: Sharpless asymmetric epoxidation / 4.2: Sharpless asymmetric epoxidation / 6.2: Wittig olefination;
DOI:10.1002/anie.200460042

Reference yield:

: 756523-94-1
7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

: 2-(tert-Butyl-dimethyl-silanyloxy)-6-((1E,3Z)-penta-1,3-dienyl)-benzoic acid (S)-1-[(2R,3S)-((Z)-3-hepta-1,6-dienyl)-oxiranylmethyl]-3-(4-methoxy-benzyloxy)-propyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: pyridine; dmap / dichloromethane / 12 h / 20 °C

2.1: acetic acid / tetrahydrofuran / 2 h / 60 °C

3.1: hydrogen; triethylamine / Lindlar's catalyst / tetrahydrofuran / 8 h / 760 Torr

4.1: titanium(IV) isopropylate; DIPT / dichloromethane / 0.5 h / -20 °C

4.2: tert-butyl hydroperoxide / 15; 23 / 16 h / -20 °C

5.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran

6.2: 13 / -10 °C

7.1: potassium carbonate / methanol / 12 h / 20 °C

8.1: sodium hexamethyldisilazane / tetrahydrofuran

8.2: 13 / 0 - 25 °C

9.1: 1H-imidazole / tetrahydrofuran

With pyridine; 1H-imidazole; titanium(IV) isopropylate; dmap; DIPT; hydrogen; sodium hexamethyldisilazane; potassium carbonate; Dess-Martin periodane; acetic acid; triethylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; 3.1: Lindlar hydrogenation / 4.1: Sharpless asymmetric epoxidation / 4.2: Sharpless asymmetric epoxidation / 6.2: Wittig olefination;
DOI:10.1002/anie.200460042