(3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate

Base Information

Chemical Name:(3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate
CAS No.:1399679-86-7
Molecular Formula:C₂₈H₄₈O₆Si
Molecular Weight:508.771
Hs Code.:

Synonyms:(3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate

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Chemical Property of (3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate

Chemical Property:

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Technology Process of (3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate

There total 9 articles about (3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate 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: 85.0%

: 1399680-24-0
(3R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-oxonon-8-enoate

: 75-16-1
methylmagnesium bromide

: 1399679-86-7
(3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 - -40 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol301886g

Reference yield:

: 1399680-18-2
(6R,7S)-tert-butyl 6-hydroxy-7-((4-methoxybenzyl)oxy)-3-oxonon-8-enoate

: 1399679-86-7
(3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: 1H-imidazole / dichloromethane / 4 h / 0 - 23 °C / Inert atmosphere

2: sodium tetrahydroborate / tetrahydrofuran / -20 °C

3: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 36 h / 23 °C / Inert atmosphere

5: tetrahydrofuran; diethyl ether / 2 h / -78 - -40 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol301886g

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 1399679-86-7
(3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: phosphorus tribromide / diethyl ether / 2 h / 0 °C

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 0 - 23 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 4 h / 0 - 23 °C / Inert atmosphere

5.1: sodium tetrahydroborate / tetrahydrofuran / -20 °C

6.1: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 36 h / 23 °C / Inert atmosphere

8.1: tetrahydrofuran; diethyl ether / 2 h / -78 - -40 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; mineral oil;
DOI:10.1021/ol301886g