(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

Base Information

Chemical Name:(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone
CAS No.:220430-23-9
Molecular Formula:C₁₈H₃₃NO₃Si
Molecular Weight:339.55
Hs Code.:

Synonyms:(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

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Chemical Property of (3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

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Technology Process of (3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

There total 3 articles about (3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-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: 60.0%

: 220430-44-4
(S)-6-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-cyclohex-1-enecarboxylic acid ethyl ester

: 220430-23-9
(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

Guidance literature:: With diisobutylaluminium hydride; In methanol; toluene; at -78 - 0 ℃;
DOI:10.3987/COM-98-8302

Reference yield:

: 28469-52-5
6-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

: 220430-23-9
(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / NBS, dimethyl sulfide / CH₂Cl₂ / 2.5 h / Ambient temperature

2: 30 percent / zinc dust / tetrahydrofuran / 1 h / 40 °C

3: 60 percent / DIBAL-H / toluene; methanol / -78 - 0 °C

With N-Bromosuccinimide; dimethylsulfide; diisobutylaluminium hydride; zinc; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.3987/COM-98-8302

Reference yield:

: 119105-31-6
6-bromocyclohex-1-enecarboxylic acid ethyl ester

: 220430-23-9
(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 2 steps

1: 30 percent / zinc dust / tetrahydrofuran / 1 h / 40 °C

2: 60 percent / DIBAL-H / toluene; methanol / -78 - 0 °C

With diisobutylaluminium hydride; zinc; In tetrahydrofuran; methanol; toluene;
DOI:10.3987/COM-98-8302