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

Base Information

• Chemical Name: 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone
• CAS No.: 115728-43-3
• Molecular Formula: C₂₇H₃₀O₃SeSi
• Molecular Weight: 509.579
• Mol file: 115728-43-3.mol

Synonyms:5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone

Chemical Property of 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone

There total 13 articles about 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone (115728-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1080/07328319808004670

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-dihydro-furan-2-one (106731-86-6,106731-87-7,115728-43-3,115728-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

With dmap; triethylamine; lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone (115728-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1080/07328319808004670

upstream raw materials:

Phenylselenyl bromide

(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

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

3'-Deoxythymidine

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>thymine