(4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one

Base Information

• Chemical Name: (4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one
• CAS No.: 333968-39-1
• Molecular Formula: C₂₂H₃₄O₃Si
• Molecular Weight: 374.596
• Mol file: 333968-39-1.mol

Synonyms:(4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one

Chemical Property of (4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one

There total 1 articles about (4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-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: 70.0%

4-benzyloxybut-1-ene (70388-33-9) + (R)-4-((tert-butyldimethylsilyl)oxy)-2-iodocyclopent-2-en-1-one (150686-70-7) → (4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one (333968-39-1)

Guidance literature:

4-benzyloxybut-1-ene; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃; for 4h;

(R)-4-((tert-butyldimethylsilyl)oxy)-2-iodocyclopent-2-en-1-one; With potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1021/ol015613a

Reference yield: 83.0%

(R)-2-(tert-butyldimethylsilyloxy)-4-iodo-1-phenoxybutane (333968-37-9) + (4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one (333968-39-1) → 2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one (333968-40-4)

Guidance literature:

(R)-2-(tert-butyldimethylsilyloxy)-4-iodo-1-phenoxybutane; With tert.-butyl lithium; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane; at -78 - -40 ℃;

(4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one; In tetrahydrofuran; diethyl ether; pentane; at -78 - -20 ℃; Further stages.;

DOI:10.1021/ol015613a

Reference yield:

(4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one (333968-39-1) → N-methyl-{4-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybutyl)cyclopentyl]butylamino}acetic acid

Guidance literature:

Multi-step reaction with 9 steps

1.1: tert-BuLi; (2-thienyl)Cu(CN)Li / pentane; diethyl ether; tetrahydrofuran / -78 - -40 °C

1.2: 83 percent / diethyl ether; tetrahydrofuran; pentane / -78 - -20 °C

2.1: L-Selectride / tetrahydrofuran / 4 h / -78 °C

3.1: 2.43 g / imidazole / dimethylformamide / 36 h / 20 °C

4.1: 89 percent / H₂ / Pd/C / ethyl acetate / 48 h / 20 °C

5.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.75 h / -78 - 0 °C

6.1: 66 percent / NaCNBH₃; Et₃N / methanol; diethyl ether / 0.17 h / 20 °C

7.1: 98 percent / NaCNBH₃ / H₂O; methanol / 0.25 h / 20 °C

8.1: H₂SiF₆ / acetonitrile; H₂O / 4 h / 20 °C

9.1: 100 percent / 1,4-cyclohexadiene / Pd/C / ethanol / 2 h / 20 °C

With 1H-imidazole; fluorosilicic acid; oxalyl dichloride; cyclohexa-1,4-diene; hydrogen; tert.-butyl lithium; L-Selectride; sodium cyanoborohydride; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; pentane; 5.1: Swern oxidation;

DOI:10.1021/ol015613a

upstream raw materials:

4-benzyloxybut-1-ene

(R)-4-((tert-butyldimethylsilyl)oxy)-2-iodocyclopent-2-en-1-one

Downstream raw materials:

2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one

{4-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybutyl)-cyclopentyl]butylthio}acetic acid

benzyl N-methyl-{4-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybutyl)cyclopentyl]butylamino}acetate

4-{3,5-bis(tert-butyldimethylsilyloxy)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]cyclopentyl}butanal