191528-75-3

Upstream product

• 191528-74-2 (2R,3aR,6S,6aS)-2-Phenyl-6-(tetrahydro-pyran-2-yloxy)-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 756-79-6 dimethyl methane phosphonate 
• 191528-73-1 (2R,3aR,6S,6aS)-6-Hydroxy-2-phenyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 

Downstream Products

• 191528-76-4 (2R,3aR,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-one 
• 191528-77-5 (2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 191528-78-6 Phosphoric acid (2R,3aR,4R,6S,6aS)-6-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester diphenyl ester 
• 191528-79-7 Morpholin-4-yl-phosphonic acid 2-cyano-ethyl ester (2R,3aR,4S,6R,6aR)-6-(diphenoxy-phosphoryloxymethyl)-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester 
• 1053252-81-5 C₃₂H₃₆N₂O₉P₂ 

Relevant academic research and scientific papers

Synthesis of (+)-(1S)-1-pyrophosphoryl-(2R, 3R)-2,3-dihydroxy-(4S)-4-(phosphoryloxymethyl)cyclopentane, a stable, optically-active carbocyclic analog of 5-phosphoribosyl-1-pyrophosphate (PRPP)

A total synthesis of the cyclopentyl analog of the important biochemical intermediate 5-phosphoribosyl-1-pyrophosphate (PRPP) is reported. The synthesis proceeds from the benzylidene acetal of D-ribonolactone to the correct enantiomeric form of the cyclopentyl PRPP analog in ca. 4% overall yield. Because of the low reactivity of the carbocyclic analog compared to PRPP, the compound should be a highly useful tool for mechanistic and crystallographic investigations of the phosphoribosyltransferases, a family of enzymes that utilizes PRPP as a substrate.