(3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one
• CAS No.: 135297-03-9
• Molecular Formula: C₁₇H₃₁NO₂Si
• Molecular Weight: 309.524
• Mol file: 135297-03-9.mol

Synonyms:(3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one

Chemical Property of (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one

There total 12 articles about (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-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: 64.0%

(3S,4R)-3-[(1R)-1-(tert-Butyldimethylsilyloxy)ethyl]-4-{[(2'R)-1'-(4-methylphenylsulfono)hydrazono]cyclohexan-2'-yl}azetidin-2-one → (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one (135297-03-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

DOI:10.1039/a605081f

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) + Cyclohex-2-enyl-bis-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane → (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one (135297-03-9) + (3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(R)-cyclohex-2-enyl-azetidin-2-one

Guidance literature:

With diethylzinc; In tetrahydrofuran; hexane; at 0 - 23 ℃; for 8h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00142a045

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) + Cyclohex-2-enyl-bis-(1,2-dimethyl-propyl)-borane → (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one (135297-03-9) + (3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(R)-cyclohex-2-enyl-azetidin-2-one

Guidance literature:

With diethylzinc; In tetrahydrofuran; hexane; at 0 ℃; for 6h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00142a045

upstream raw materials:

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-2-oxo-cyclohexyl)-azetidin-2-one

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

1-(Trimethylsilyloxy)cyclohexene

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone

Downstream raw materials:

{(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester

5-(benzyloxycarbonyl-methyl-amino)-1-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

GV129606