1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose

Base Information

• Chemical Name: 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose
• CAS No.: 189818-64-2
• Molecular Formula: C₂₉H₃₄O₄SeSi
• Molecular Weight: 553.632
• Mol file: 189818-64-2.mol

Synonyms:1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose

Chemical Property of 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose

There total 10 articles about 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose 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: 98.0%

acetic anhydride (108-24-7) + (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-ol → 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose (189818-64-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; 1.) 0 deg C, 1 h, 2.) room temperature, 12 h;

DOI:10.1021/jo970177k

Reference yield:

(R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one (128075-94-5) → 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose (189818-64-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiHMDS; Me₃SiCl / tetrahydrofuran / 0.5 h / -78 °C

1.2: 62.6 percent / tetrahydrofuran / -78 °C

2.1: DIBAL-H / toluene / 1.5 h / -78 °C

3.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; chloro-trimethyl-silane; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene; 1.1: silylation / 1.2: Substitution / 2.1: Reduction / 3.1: Acetylation;

DOI:10.1080/07328319908044642

Reference yield:

5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-L-erythro-pentonic acid-γ-lactone (189818-62-0) → 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose (189818-64-2)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / toluene / 1.5 h / -78 °C

2: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; diisobutylaluminium hydride; triethylamine; In dichloromethane; toluene; 1: Reduction / 2: Acetylation;

DOI:10.1080/07328319908044642

upstream raw materials:

acetic anhydride

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

(R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one

tert-butylchlorodiphenylsilane

Downstream raw materials:

9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-L-erythro-pentofuranosyl]-6-chloro-9H-purine

4-Amino-1-[(2S,3S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidin-2-one

β-L-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)uridine

2-Amino-9-[(2S,3S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one