(+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

Base Information

Chemical Name:(+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone
CAS No.:143159-97-1
Molecular Formula:C₂₂H₂₅NO₄
Molecular Weight:367.445
Hs Code.:

Synonyms:(+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

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Chemical Property of (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

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Technology Process of (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

There total 8 articles about (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone 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: 63.0%

: 19810-31-2
Benzyloxyacetyl chloride

: 100-46-9
benzylamine

: 5736-03-8
(d,l) isopropylidene glyceraldehyde

: 143159-97-1
(+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

Guidance literature:: benzylamine; (d,l) isopropylidene glyceraldehyde; With magnesium sulfate; In dichloromethane; at 20 ℃;

Benzyloxyacetyl chloride; With triethylamine; In dichloromethane; at 20 ℃; Further stages.;
DOI:10.1021/jo991984h

Reference yield:

: 100777-91-1
(2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine

: 19810-31-2
Benzyloxyacetyl chloride

: 143159-97-1
(+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

Guidance literature:: With triethylamine; for 0.05h; Yield given; Irradiation;
DOI:10.1016/S0040-4039(00)92513-9

Reference yield:

: 52373-72-5
methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

: 143159-97-1
(+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

Guidance literature:: Multi-step reaction with 3 steps

1: DIBAL-H / toluene; hexane / 2 h / -78 °C

2: 4A MS / CH₂Cl₂ / 1 h / 0 °C

3: Et₃N / CH₂Cl₂ / 20 °C

With diisobutylaluminium hydride; triethylamine; In hexane; dichloromethane; toluene;
DOI:10.1021/jo001786m