3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone

Base Information

• Chemical Name: 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone
• CAS No.: 729596-46-7
• Molecular Formula: C₂₀H₁₈O₇
• Molecular Weight: 370.359
• Mol file: 729596-46-7.mol

Synonyms:3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone

Chemical Property of 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

((2R,3R,4R)-3-(Benzoyloxy)-4-hydroxy-4-methyl-5-oxotetrahydrofuran-2-yl)methylbenzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone

There total 1 articles about 3,5-di-O-benzoyl-2-C-methyl-D-ribono-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: 90.5%

2-C-methyl-D-ribono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7) + benzoyl chloride (98-88-4) → 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone (729596-46-7)

Guidance literature:

With pyridine; at 20 ℃; for 5h; Temperature; Cooling with ice;

Reference yield: 99.0%

3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone (729596-46-7) + trifluoromethylsulfonic anhydride (358-23-6) → ((2R,3R,4R)-3-(benzoyloxy)-4-methyl-5-oxo-4-(((trifluoromethyl)sulfonyl)oxy)tetrahydrofuran-2-yl)methylbenzoate

Guidance literature:

3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone; With pyridine; In dichloromethane; at -10 ℃; for 0.0833333h;

trifluoromethylsulfonic anhydride; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2015.05.085

Reference yield: 85.0%

3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone (729596-46-7) + methanesulfonyl chloride (124-63-0) → ((2R,3R,4R)-3-(benzoyloxy)-4-methyl-4-((methylsulfonyl)oxy)-5-oxotetrahydrofuran-2-yl)methylbenzoate

Guidance literature:

With triethylamine; In dichloromethane; Cooling with ice;

upstream raw materials:

2-C-methyl-D-ribono-1,4-lactone

benzoyl chloride

Downstream raw materials:

1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose

3,5-di-O-benzoyl-2-C-methyl-D-ribofuranose

((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate

((2R,3R,4S)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methylbenzoate

Refernces

• 1、 Lv, Bingqing,Guo, Shuang,Zhu, Fuqiang,Hu, Tianwen,Guo, Qi,Lin, Haixia,Xie, Yuanchao,Shen, Jingshan. "Facile synthesis of 2-C-methyl-D-arabino-γ-1,4-lactones and mechanism study". supporting information. p. 1473 - 1475. Retrieved 2018/03/13.
• 2、 Xie, Yuanchao,Zhang, Jian,Tian, Guanghui,Xu, Mingshuo,Hu, Tianwen,Jiang, Xiangrui,Shen, Jingshan. "A neighboring group participation strategy: Facile synthesis of 3,5-di-O-benzoyl-2-C-methyl-d-arabino-γ-lactone". supporting information. p. 4345 - 4348. Retrieved 2015/06/22.