2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

Base Information

Chemical Name:2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole
CAS No.:1404078-84-7
Molecular Formula:C₄₂H₆₁NO₈Si
Molecular Weight:736.034
Hs Code.:

Synonyms:2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

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Chemical Property of 2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

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Technology Process of 2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

There total 14 articles about 2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole 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: 34.0%

: 1361332-32-2
2-[(S)-8-hydroxy-7-((S)-2-methylbutyl)-1-oxoisochroman-3-yl]acetaldehyde

: 1404078-82-5
2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

: 1404078-83-6
2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

: 1404078-84-7
2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

Guidance literature:: 2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1h; Inert atmosphere;

With dimethyl zinc(II); In diethyl ether; toluene; pentane; at -78 ℃; for 0.25h;

2-[(S)-8-hydroxy-7-((S)-2-methylbutyl)-1-oxoisochroman-3-yl]acetaldehyde; In diethyl ether; toluene; pentane; at -78 ℃; for 3h;
DOI:10.1039/c2ob26256h

Reference yield:

: 627511-81-3
(2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentanal

: 1404078-84-7
2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

Guidance literature:: Multi-step reaction with 10 steps

1.1: titanium tetrachloride / dichloromethane / 0.33 h / -50 °C

1.2: 2 h / -40 °C

1.3: 2 h / -78 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 - 20 °C

3.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 - 20 °C

4.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C

4.2: 72 h / 20 °C

5.1: diethylamino-sulfur trifluoride / dichloromethane / 2 h / -78 °C

6.1: copper(ll) bromide; hexamethylenetetramine; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C

7.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.75 h / -78 °C

8.1: potassium carbonate / methanol / 0 - 20 °C

9.1: Schwartz's reagent / tetrahydrofuran / 1 h / 0 °C

9.2: 0.67 h / -78 °C / Darkness

10.1: tert.-butyl lithium / pentane; diethyl ether / 1 h / -78 °C / Inert atmosphere

10.2: 0.25 h / -78 °C

10.3: 3 h / -78 °C

With 2,6-dimethylpyridine; Schwartz's reagent; diethylamino-sulfur trifluoride; hexamethylenetetramine; dihydrogen peroxide; tert.-butyl lithium; titanium tetrachloride; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; copper(ll) bromide; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; pentane;
DOI:10.1039/c2ob26256h

Reference yield:

: (3S,4R,5R)-3-(tert-butyldimethylsilyloxy)-1-[(R)-4-isopropyl-2-thioxothiazolidin-3-yl]-5-(4-methoxybenzyloxy)-4-methylheptan-1-one

: 1404078-84-7
2-{(2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-4-[(4-methoxybenzyl)oxy]-3-methylhexyl}-4-[(E)-2-iodovinyl]oxazole

Guidance literature:: Multi-step reaction with 8 steps

1.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C

2.2: 72 h / 20 °C

3.1: diethylamino-sulfur trifluoride / dichloromethane / 2 h / -78 °C

4.1: copper(ll) bromide; hexamethylenetetramine; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.75 h / -78 °C

6.1: potassium carbonate / methanol / 0 - 20 °C

7.1: Schwartz's reagent / tetrahydrofuran / 1 h / 0 °C

7.2: 0.67 h / -78 °C / Darkness

8.1: tert.-butyl lithium / pentane; diethyl ether / 1 h / -78 °C / Inert atmosphere

8.2: 0.25 h / -78 °C

8.3: 3 h / -78 °C

With Schwartz's reagent; diethylamino-sulfur trifluoride; hexamethylenetetramine; dihydrogen peroxide; tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; copper(ll) bromide; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; pentane;
DOI:10.1039/c2ob26256h