What is 2,3,5-Tri-O-benzyl-D-ribonolactone?

Identification

Product Name:    2,3,5-Tri-O-benzyl-D-ribonolactone    

Synonyms:    1-Chloro-3,5-di-(p-chlorobenzoyl)-2-deoxy-D-ribofuranose;2,3,5-Tri-O-benzyl-D-ribono-1,4-lactone;2,3,5-TRI-O-BENZYL-D-RIBONOLACTONE;(3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxyMethyl)-dihydrofuran-2(3H)-one;2,3,5-Tris-O-(phenylmethyl)-D-ribonic acid γ-lactone;(3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolan-2-one;2,2,5-tri-O-benzyl-D-ribono-1,4-lancton;2,3,5-Tri-O-benzyl-D-ribonic Acid 1,4-lactone

CAS:    55094-52-5    

MF:    C26H26O5

MW:    418.48

Structure 

Properties

Melting point     54-55 °C    

Boiling point     576.8±50.0 °C(Predicted)    

Density     1.21±0.1 g/cm3(Predicted)

Application

2,3,5-Tri-O-benzyl-D-ribono-1,4-lactone is a synthetic building block which can undergo reaction with nucleophilic carbon species to afford C-ribosides (via the corresponding hemiacetal).  Treatment of 2,3,5-Tri-O-benzyl-D-ribono-1,4-lactone with stronger reducing agents, such as sodium borohydride, affords ring opened products with a stereo-defined poly-oxygenated carbon chain backbone.