ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate

Base Information

• Chemical Name: ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate
• CAS No.: 1039456-14-8
• Molecular Formula: C₂₂H₃₆O₅Si
• Molecular Weight: 408.61

Synonyms:ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate

Chemical Property of ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate

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Technology Process of ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate

There total 1 articles about ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate 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: 70.0%

(R,E)-ethyl 7-(tert-butyldimethylsilyloxy)-5-hydroxyhept-2-enoate (1039456-13-7) + benzaldehyde (100-52-7) → ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1039456-14-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; optical yield given as %de; diastereoselective reaction;

DOI:10.1021/ol801055b

Reference yield: 93.0%

ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1039456-14-8) → ethyl 2-((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1039456-36-4)

Guidance literature:

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

DOI:10.1021/ol801055b

Reference yield: 89.0%

ethyl 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1039456-14-8) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)-N-methoxy-N-methylacetamide (1039456-28-4)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -20 ℃; for 0.5h;

DOI:10.1021/ol801055b

upstream raw materials:

(R,E)-ethyl 7-(tert-butyldimethylsilyloxy)-5-hydroxyhept-2-enoate

benzaldehyde

Downstream raw materials:

ethyl 2-((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)acetate

2-((2S,4S,6S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)-N-methoxy-N-methylacetamide

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