104945-87-1

Upstream product

• 5336-08-3 D-Ribono-1,4-lactone 
• 100-52-7 benzaldehyde 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 134877-40-0 3,4-O-benzylidene-D-ribonic-δ-lactone 
• 20603-45-6 3,4-O-Benzylidene-D-(+)-ribonic acid δ-lactone 

Downstream Products

• 146918-99-2 3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone 
• 134790-11-7 ((3aR,7R,7aS)-6-Oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-carbamic acid benzyl ester 
• 134790-12-8 (5S)-(5-hydroxymethyl-2-oxo-2,5-dihydrofuran-3-yl)carbamic acid benzyl ester 
• 147410-09-1 2-Amino-2-deoxy-3,4-O-benzylidene-1,5-D-ribonolactone 
• 97551-67-2 (3S,5S)-3-benzyloxycarbonylamino-5-hydroxy-γ-lactone 
• 134877-41-1 2-Azido-2-deoxy-3,4-O-benzylidene-1,5-D-ribonolactone 
• 815626-14-3 2-azido-3,4-O-benzylidene-2-deoxy-D-arabinono-1,5-lactone 
• 605668-38-0 methyl 2,5-anhydro-D-arabinoate 

Relevant academic research and scientific papers

SYNTHESIS OF 2R,3S,4R-DIHYDROXYPROLINE FROM D-RIBONOLACTONE

A synthesis of 2R,3S,4R-dihydroxyproline is described in which an azide is introduced into C-2 position of D-ribonolactone with retention of configuration.

Synthesis of highly functionalized chiral nitriles by radical fragmentation of β-hydroxy azides. Convenient transformation of aldononitriles into 1,4- and 1,5-iminoalditols

The synthesis of highly functionalized nitriles by an alkoxyl radical fragmentation of cyclic β-hydroxy azides is described. The alkoxyl radicals were generated by reaction of the alcohols with (diacetoxyiodo)benzene and iodine under mild conditions compa

An efficient and concise entry to (-)-4,5-dihydroxy-d-threo-l norvaline. Formal synthesis of clavalanine

The title amino acid (2) has been synthesized for the first time in a seven-step sequence from D-ribonolactone, in 20% overall yield. Since the N-carbamoyl derivative of (2) in its y-lactone form has been used to prepare clavalanine, a formal total synthe

Synthesis of (2R,3S,4R)-3,4-Dihydroxyproline from D-Ribonolactone; an Approach to the Synthesis of Polyfunctionalised D-Amino Acids from Sugar Lactones. X-Ray Molecular Structures of 2-Azido-3,4-O-(R)-benzylidene-2-deoxy-D-ribono-1,5-lactone, 2-Azido-2-deoxy-D-ribono-1,4-lactone, and ...

A general approach to the synthesis of polyfunctionalised amino acids from sugar lactones, in wich nucleophilic displacement by azide ion of O-trifluoromethanesulphonyl esters adjacent to the lactone carbonyl is the key step, is discussed and is exemplified by the synthesis of the D-amino acid (2R,3S,4R)-3,4-dihydroxyproline from d-ribonolactone; unexpectedly, displacement of a triflate by azide in the C-2 position of ribonolactone occurs with retention of configuration.The X-ray crystal structures of 2-azido-3,4-O-(R)-benzylidene-2-deoxy-D-ribono-1,5-lactone, 2-azido-2-deoxy-D-ribono-1,4-lactone, and (2R,3S,4R)-3,4-dihydroxyproline are reported.I.r. spectroscopy does not discriminate reliably between 1,4-and 1,5-lactones, and X-ray crystallography is necessary to provide reliable structural information in this area.