Compound Q&A
How is (1R,4R,5S)-4-(2-Chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione (CAS: 437742-34-2) typically synthesized?
Answer
![(1R,4R,5S)-4-(2-Chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione](https://static.chemtradehub.com/structs/437/437742-34-2-8ec6.webp "(1R,4R,5S)-4-(2-Chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione")
This compound can be synthesized via a multi-step process involving the protection of a hydroxyl group, alkylation, cyclization, and deprotection. Commonly used catalysts include tin(II) chloride and sodium hydride. The reaction typically yields 80-85% of the target compound with good regioselectivity. Detailed procedures are available in organic synthesis literature.
About
CAS No
437742-34-2
English Name
(1R,4R,5S)-4-(2-Chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
Molecular Formula
C15H20ClNO4
Molecular Weight
313.78 g/mol
SMILES
C[C@]12[C@H](C(=O)N[C@]1(C(=O)O2)[C@H]([C@H]3CCCC=C3)O)CCCl
InChIKey
NGWSFRIPKNWYAO-SHTIJGAHSA-N
Last Updated: 2025-11-01 22:12
![(1R,4R,5S)-4-(2-Chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione — ShenZhenAiTaHuaXue Co Ltd](https://static.chemtradehub.com/suppliers/67ced0fb2b2de6e8e95a67fa/67ced0fb2b2de6e8e95a67fa-logo.webp){kind=logo}
![(1R,4R,5S)-4-(2-Chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione — ShenZhenZhenJiangShengWuJiShu Co Ltd](https://static.chemtradehub.com/suppliers/67cec9142b2de6e8e95a51e7/67cec9142b2de6e8e95a51e7-logo.webp){kind=logo}