(2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde

Base Information

Chemical Name:(2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde
CAS No.:1351977-04-2
Molecular Formula:C₂₃H₃₈O₅Si
Molecular Weight:422.637
Hs Code.:

Synonyms:(2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde

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Chemical Property of (2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde

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Technology Process of (2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde

There total 9 articles about (2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde 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:

: C₂₃H₄₀O₅Si

: C₂₃H₃₈O₅Si

: 1351977-04-2
(2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 23 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol203130b

Reference yield:

: 1351977-03-1
C₂₃H₄₀O₅Si

: 1351977-04-2
(2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1002/chem.201302197

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 1351977-04-2
(2S,3R)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-methylpentan-2-yl)-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium hydroxide / dimethyl sulfoxide / 4 h / 0 °C

2.1: butyraldehyde; C₅₃H₄₃IrNO₈P₂ / chlorobenzene / 72 h / 50 °C / Sealed tube

3.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -40 °C

4.1: osmium(VIII) oxide / water; 1,4-dioxane; tert-butyl alcohol / 0.17 h / 20 °C

4.2: 5 h / 20 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

5.2: 4.5 h / -78 - 20 °C

6.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C

7.1: D-(-)-diisopropyl tartrate; titanium(IV)isopropoxide; tert.-butylhydroperoxide / dichloromethane / -20 °C / Molecular sieve

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; osmium(VIII) oxide; C₅₃H₄₃IrNO₈P₂; sodium hexamethyldisilazane; titanium(IV)isopropoxide; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; Dess-Martin periodane; butyraldehyde; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; chlorobenzene; tert-butyl alcohol;
DOI:10.1002/chem.201302197