(4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one

Base Information

Chemical Name:(4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one
CAS No.:911423-80-8
Molecular Formula:C₂₆H₄₁NO₆Si
Molecular Weight:491.7
Hs Code.:

Synonyms:(4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one

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Chemical Property of (4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one

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Technology Process of (4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one

There total 7 articles about (4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one 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: 76.0%

: 911423-79-5
3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoic acid

: (4S,5R)-4-methyl-5-phenyl-1,3-oxazolidin-2-one lithium salt

: 911423-80-8
(4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one

Guidance literature:: 3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoic acid; With pivaloyl chloride; triethylamine; In diethyl ether; at -78 - -30 ℃; for 0.5h;

(4S,5R)-4-methyl-5-phenyl-1,3-oxazolidin-2-one lithium salt; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 3h;
DOI:10.1002/ejoc.200600113

Reference yield:

: 3-[(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propionaldehyde

: 911423-80-8
(4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / NaH₂PO₄; NaClO₂; 2,3-dimethyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 20 °C

2.1: triethylamine; pivaloyl chloride / diethyl ether / 0.5 h / -78 - -30 °C

2.2: 76 percent / diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C

With sodium chlorite; sodium dihydrogenphosphate; 2,3-Dimethyl-2-butene; pivaloyl chloride; triethylamine; In diethyl ether; water; tert-butyl alcohol;
DOI:10.1002/ejoc.200600113

Reference yield:

: 911423-78-4
3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propan-1-ol

: 911423-80-8
(4S,5R)-3-(3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl)-4-methyl-5-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

2.1: 93 percent / NaH₂PO₄; NaClO₂; 2,3-dimethyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 20 °C

3.1: triethylamine; pivaloyl chloride / diethyl ether / 0.5 h / -78 - -30 °C

3.2: 76 percent / diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 2,3-Dimethyl-2-butene; pivaloyl chloride; Dess-Martin periodane; triethylamine; In diethyl ether; dichloromethane; water; tert-butyl alcohol;
DOI:10.1002/ejoc.200600113