(2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

Base Information

Chemical Name:(2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate
CAS No.:1586033-49-9
Molecular Formula:C₂₉H₄₄O₅Si
Molecular Weight:500.751
Hs Code.:

Synonyms:(2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

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Chemical Property of (2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

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Technology Process of (2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

There total 4 articles about (2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate 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:

: 1586033-48-8
(R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)undec-2-enoate

: 1586033-49-9
(2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

: (2S,3R,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; at 20 ℃; for 12h; Overall yield = 90 %; Overall yield = 8.1 g; Inert atmosphere;
DOI:10.1016/j.tet.2014.02.072

Reference yield:

: 1586033-59-1
C₉H₁₈O₂

: 1586033-49-9
(2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

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

2.2: 0 - 20 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tet.2014.02.072

Reference yield:

: 1586033-47-7
(R)-2-(tert-butyldiphenylsilyloxy)nonanal

: 1586033-49-9
(2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 0 - 20 °C / Inert atmosphere

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tet.2014.02.072