5-{1-[(Diphenylsilyl)oxy]-2,2-dimethylpropyl}oxolan-2-one

Base Information

• Chemical Name: 5-{1-[(Diphenylsilyl)oxy]-2,2-dimethylpropyl}oxolan-2-one
• CAS No.: 128075-94-5
• Molecular Formula: C21H26O3Si
• Molecular Weight: 354.521
• DSSTox Substance ID: DTXSID60721461
• Mol file: 128075-94-5.mol

Synonyms:128075-94-5;DTXSID60721461;5-{1-[(Diphenylsilyl)oxy]-2,2-dimethylpropyl}oxolan-2-one

Chemical Property of 5-{1-[(Diphenylsilyl)oxy]-2,2-dimethylpropyl}oxolan-2-one

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 353.15729619
• Heavy Atom Count: 25
• Complexity: 415

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(C1CCC(=O)O1)O[Si](C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of 5-{1-[(Diphenylsilyl)oxy]-2,2-dimethylpropyl}oxolan-2-one

There total 7 articles about 5-{1-[(Diphenylsilyl)oxy]-2,2-dimethylpropyl}oxolan-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: 95.0%

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) + tert-butylchlorodiphenylsilane (58479-61-1) → (R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one (128075-94-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2008.10.034

Reference yield: 66.0%

(S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclobutanone (135253-29-1) → (R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one (128075-94-5)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In methanol; for 2h;

DOI:10.1016/S0957-4166(00)80211-6

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one (128075-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / NaNO₂; HCl / H₂O / -5 - 20 °C

2: 53 percent / BH₃*Me₂S / tetrahydrofuran / -20 - 20 °C

3: 94 percent / imidazole / dimethylformamide / 1 h / 20 °C

With 1H-imidazole; hydrogenchloride; dimethylsulfide borane complex; sodium nitrite; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.06.105

upstream raw materials:

(S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclobutanone

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

tert-butylchlorodiphenylsilane

D-Glutamic acid

Downstream raw materials:

5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-L-erythro-pentonic acid-γ-lactone

(3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-dihydro-furan-2-one

(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-ol

(2S,4R)-5-(t-butyldiphenylsiloxy)-2-fluoropentan-4-olide