ethyl (R)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate

Base Information

• Chemical Name: ethyl (R)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate
• CAS No.: 1187242-50-7
• Molecular Formula: C₂₂H₃₆O₅Si
• Molecular Weight: 408.61

Synonyms:ethyl (R)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate

Chemical Property of ethyl (R)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate

Chemical Property:

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Technology Process of ethyl (R)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate

There total 1 articles about ethyl (R)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate 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: 60.0%

ethyl (E)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]acrylate (1187242-48-3) + methylmagnesium bromide (75-16-1) → ethyl (R)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate (1187242-50-7) + ethyl (S)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate (1187242-74-5)

Guidance literature:

methylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -78 - -40 ℃; Inert atmosphere;

ethyl (E)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]acrylate; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; pH=9; optical yield given as %de;

DOI:10.1016/j.tet.2009.06.029

Reference yield: 73.0%

ethyl (R)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]butylate (1187242-50-7) → (2S,4R,8R,9R)-8-methyl-2-phenylhexahydropyrano[3,2-d]-1,3-dioxin-6-one (1187242-52-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.06.029

upstream raw materials:

ethyl (E)-3-[(2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl]acrylate

methylmagnesium bromide

Downstream raw materials:

(2S,4R,8R,9R)-8-methyl-2-phenylhexahydropyrano[3,2-d]-1,3-dioxin-6-one

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