(3S,4S)-(-)-1-BENZYL-3,4-DIHYDROXYPYRROLIDIN-2,5-DIONE

Base Information

• Chemical Name: (3S,4S)-(-)-1-BENZYL-3,4-DIHYDROXYPYRROLIDIN-2,5-DIONE
• CAS No.: 187032-53-7
• Molecular Formula: C11H11 N O4
• Molecular Weight: 221.213
• Mol file: 187032-53-7.mol

Synonyms:2,5-Pyrrolidinedione,3,4-dihydroxy-1-(phenylmethyl)-, (3S-trans)-

Chemical Property of (3S,4S)-(-)-1-BENZYL-3,4-DIHYDROXYPYRROLIDIN-2,5-DIONE

Chemical Property:

• Melting Point: 194-197 °C(Solv: ethanol (64-17-5))
• Boiling Point: 489.3±45.0 °C(Predicted)
• PKA: 11.11±0.40(Predicted)
• PSA: 77.84000
• Density: 1.525±0.06 g/cm3(Predicted)
• LogP: -0.78490

Purity/Quality:

98% purity ^*data from raw suppliers

(3S,4S)-1-Benzyl-3,4-dihydroxypyrrolidine-2,5-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4S)-(-)-1-BENZYL-3,4-DIHYDROXYPYRROLIDIN-2,5-DIONE

There total 1 articles about (3S,4S)-(-)-1-BENZYL-3,4-DIHYDROXYPYRROLIDIN-2,5-DIONE 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: 93.0%

D-tartaric acid (147-71-7,138508-61-9) + benzylamine (100-46-9) → (3S,4S)-1-N-benzyl-3,4-dihydroxypyrrolidine-2,6-dione (187032-53-7)

Guidance literature:

D-tartaric acid; benzylamine; In methanol; water; at 50 ℃;

In xylene; at 190 ℃; for 8h;

DOI:10.1016/j.tet.2006.11.047

Reference yield: 99.0%

(3S,4S)-1-N-benzyl-3,4-dihydroxypyrrolidine-2,6-dione (187032-53-7) → (3R,4R)-1-benzyl-3,4-pyrrolidinediol (163439-82-5,330152-66-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 12h; Heating;

DOI:10.1016/j.tetlet.2005.10.005

Reference yield: 86.59%

(3S,4S)-1-N-benzyl-3,4-dihydroxypyrrolidine-2,6-dione (187032-53-7) → (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol (90365-74-5,330152-66-4)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 70 ℃; for 3h;

DOI:10.1016/j.bmcl.2017.04.078

upstream raw materials:

D-tartaric acid

benzylamine

Downstream raw materials:

(3R,4R)-1-benzyl-3,4-pyrrolidinediol

(3R,4R)-1-N-benzyl-3-(4,4'-dimethoxytrityloxy)-4-hydroxypyrrolidine

(3R,4R)-1-N-benzyl-4-(4,4'-dimethoxytrityloxy)-3-mesyloxy-pyrrolidine

(3R,4R)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine

Refernces

• 1、 Kasturi, Sivaprasad,Surarapu, Sujatha,Uppalanchi, Srinivas,Anireddy, Jaya Shree,Dwivedi, Shubham,Anantaraju, Hasitha Shilpa,Perumal, Yogeeswari,Sigalapalli, Dilep Kumar,Babu, Bathini Nagendra,Ethiraj, Krishna S.. "Synthesis and α-glucosidase inhibition activity of dihydroxy pyrrolidines". supporting information. p. 2818 - 2823. Retrieved 2017/05/29.
• 2、 Seneviratne, Uthpala,Antsypovich, Sergey,Goggin, Melissa,Dorr, Danae Quirk,Guza, Rebecca,Moser, Adam,Thompson, Carrie,York, Darrin M.,Tretyakova, Natalia. "Exocyclic deoxyadenosine adducts of 1,2,3,4-diepoxybutane: Synthesis, structural elucidation, and mechanistic studies". scheme or table. p. 118 - 133. Retrieved 2011/02/16.