(4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Base Information

Chemical Name:(4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
CAS No.:317855-33-7
Molecular Formula:C₁₆H₁₉NO₅
Molecular Weight:305.331
Hs Code.:

Synonyms:(4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

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Chemical Property of (4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

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Technology Process of (4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

There total 8 articles about (4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-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: 74.0%

: 317855-09-7
(4R)-3-benzyl-4-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one

: 317855-33-7
(4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 2.5h;
DOI:10.1021/jo0012748

Reference yield:

: 79060-23-4
(2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

: 317855-33-7
(4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 61 percent / t-BuOOH; Ti(Oi-Pr)4; diisopropyl L-(+)-tartrate / CH₂Cl₂ / -30 °C

2: 92 percent / (i-Pr)2NEt / benzene / 60 °C

3: 84 percent / potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 0 °C

4: 64 percent / Amberlyst 15 resin / acetone / 18 h / 20 °C

5: 74 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 2.5 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; L-(+)-diisopropyl tartrate; Amberlyst 15 resin; potassium tert-butylate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetone; tert-butyl alcohol; benzene; 1: Sharpless asymmetric epoxidation / 5: Swern oxidation;
DOI:10.1021/jo0012748

Reference yield:

: 80581-19-7
((2S,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol

: 317855-33-7
(4S,5R)-5-[(4R)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / (i-Pr)2NEt / benzene / 60 °C

2: 84 percent / potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 0 °C

3: 64 percent / Amberlyst 15 resin / acetone / 18 h / 20 °C

4: 74 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 2.5 h / -78 °C

With oxalyl dichloride; Amberlyst 15 resin; potassium tert-butylate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetone; tert-butyl alcohol; benzene; 4: Swern oxidation;
DOI:10.1021/jo0012748