(4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one

Base Information

Chemical Name:(4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one
CAS No.:317855-12-2
Molecular Formula:C₁₆H₂₀ClNO₄
Molecular Weight:325.792
Hs Code.:

Synonyms:(4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one

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Chemical Property of (4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one

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Technology Process of (4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one

There total 8 articles about (4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-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: 83.0%

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

: 317855-12-2
(4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one

Guidance literature:: With tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 - 60 ℃; for 16h;
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

: 317855-12-2
(4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one

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: 83 percent / CCl₄; HMPT / tetrahydrofuran / 16 h / -78 - 60 °C

With tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; Amberlyst 15 resin; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetone; tert-butyl alcohol; benzene;
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

: 317855-12-2
(4R)-3-benzyl-4-[(4R,5S)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one

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: 83 percent / CCl₄; HMPT / tetrahydrofuran / 16 h / -78 - 60 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; L-(+)-diisopropyl tartrate; Amberlyst 15 resin; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetone; tert-butyl alcohol; benzene; 1: Sharpless asymmetric epoxidation;
DOI:10.1021/jo0012748