(1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone

Base Information

Chemical Name:(1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone
CAS No.:1598377-58-2
Molecular Formula:C₂₇H₄₃ClO₄Si₂
Molecular Weight:523.26
Hs Code.:

Synonyms:(1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone

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Chemical Property of (1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone

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Technology Process of (1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone

There total 4 articles about (1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone 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: 44.0%

: 1598377-54-8
(1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1R)-1-hydroxy-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone

: 1598377-58-2
(1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone

Guidance literature:: With N-chloro-succinimide; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jm500175z

Reference yield:

: 1598377-47-9
C₂₇H₄₂O₅Si₂

: 1598377-58-2
(1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone

Guidance literature:: Multi-step reaction with 2 steps

1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2: N-chloro-succinimide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; N-chloro-succinimide; cerium(III) chloride heptahydrate; triphenylphosphine; In tetrahydrofuran; methanol;
DOI:10.1021/jm500175z

Reference yield:

: 53317-09-2
9-benzyl-9-borabicyclo[3.3.1]nonane

: 1598377-58-2
(1R,4R,5R)-1,4-di-(tert-butyldimethylsilyloxy)-3-[(1S)-1-chloro-2-phenyl]ethylcyclohex-2-en-1,5-carbolactone

Guidance literature:: Multi-step reaction with 3 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; tetrahydrofuran / 4 h / 55 °C

2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3: N-chloro-succinimide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; potassium phosphate; N-chloro-succinimide; cerium(III) chloride heptahydrate; triphenylphosphine; In tetrahydrofuran; methanol; water; 1: |Suzuki Coupling;
DOI:10.1021/jm500175z