1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose

Base Information

• Chemical Name: 1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose
• CAS No.: 202272-29-5
• Molecular Formula: C₂₃H₂₉FO₄Si
• Molecular Weight: 416.565
• Mol file: 202272-29-5.mol

Synonyms:1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose

Chemical Property of 1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose

There total 3 articles about 1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-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: 99.0%

acetic anhydride (108-24-7) + 5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose (202272-28-4) → 1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose (202272-29-5)

Guidance literature:

With dmap; In dichloromethane; Ambient temperature;

DOI:10.1021/jo9717898

Reference yield:

(R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one (128075-94-5) → 1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose (202272-29-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / N-fluorodibenzenesulfonimide, LiHMDS / tetrahydrofuran / 3 h / -78 °C

2: 98 percent / DIBALH / tetrahydrofuran; hexane / 3 h / -78 °C

3: 99 percent / DMAP / CH₂Cl₂ / Ambient temperature

With dmap; diisobutylaluminium hydride; N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo9717898

Reference yield:

(2S,4R)-5-(t-butyldiphenylsiloxy)-2-fluoropentan-4-olide (202272-27-3) → 1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose (202272-29-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / DIBALH / tetrahydrofuran; hexane / 3 h / -78 °C

2: 99 percent / DMAP / CH₂Cl₂ / Ambient temperature

With dmap; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo9717898

upstream raw materials:

acetic anhydride

5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose

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

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

Downstream raw materials:

(L)-5’-O-(t-butyldiphenylsilyl)-2’,3-dideoxy-2’-fluoro-5-fluorocytidine

(L)-5’-O-(t-butyldiphenylsilyl)-2’,3’-dideoxy-2’fluoro-5-fluorouridine

(L)-5’-O-(t-butyldiphenylsilyl)-2’,3’-dideoxy-2’-fluoro-thymidine