New Cyclic Derivatives of 3′‐Amino‐3′‐deoxy‐adenosine‐5′‐diphosphate, ‐triphosphate, and ‐methylenebis(phosphonate)

Abstract

COMMUNICATIONS tone enolates to x,P-unsaturated aldehydes. The present carbene route offers an attractive alternative to this otherwise generally difficult 231 Exper imen tal Pro cediire lob: To a cooled ( -80 C ) solution o f 3 b (1.44 g, 2.68 mmol) in T H F (30 niL) was added a 2.5 M solution of BuLi in hexane (1.15 mL. 2.8 mmol) under nitrogen and the mixture was stirred at -80 C for 1 h and between -80 -C and room temperature for 0.5 h. After ieinoval of the solvents in vacuo : I solution of NaOMe (ca. 0.5 M) in MeOH (20 mL) was added and the mixture &as stirred at room temperature for 3 h. MeOH was removed and the residue was purified by column chromatography (silica gel. hexane' Et,O. 4 : l ) to give 0.83 g (76%) of9b. To a solution of 9b (0.75 g.

Binding of Nucleotides to Nucleoside Diphosphate Kinase: A Calorimetric Study

“…Most nucleoside diphosphates were purchased from Sigma. AZT-DP and 3‘-amino-3‘-deoxyADP were obtained as previously described ( , ). 3‘-deoxyADP was prepared by chemical phosphorylation of the nucleoside.…”

One-Pot Carbanionic Synthesis of P1,P2-Diglycosyl, P1,P1,P2-Triglycosyl, and P1,P1,P2,P2-Tetraribosyl Methylenediphosphonates

“…Pankiewicz et al suggest an interesting process with nucleoside bicyclic trisanhydrides found in the reaction between nucleoside 5‘-methylenediphosphonates and DCC. Thus, the reaction of the trisanhydride derivative of 2‘,3‘- O -isopropylideneadenosin-5‘-yl with 2‘,3‘- O -isopropylidenetiazofurin leads to the β-methylene-TAD in 92% overall yield 10a. The method has been recently used in the synthesis of MAD 6a.…”

“…To the best of our knowledge, only the synthesis of nucleoside methylenediphosphonate sugars or dinucleoside methylenediphosphonates is documented. , As part of our program in the synthesis of analogues of natural glycosyl-disubstituted pyrophosphates, we have recently described preliminary results on the one-pot alkylidene diphosphorylation of 2,3- O -isopropylidene uridine or 2,3:5,6-di- O -isopropylidene- d -mannofuranose to synthesize the methylenediphosphonate analogues of natural P 1 , P 2 -glycosyl-disubstituted pyrophosphates …”

Synthesis and stability studies of phosphonoformate–amino acid conjugates: a new class of slowly releasing foscarnet prodrugs

“…To form the P-N linkage, we chose EDC-promoted coupling of 2 with C-ethyl protected l-amino acids (Val, Leu, or Phe) in aqueous solution under neutral to slightly alkaline conditions. 25 The intermediate 2 was obtained by quantitative and regioselective silyldealkylation of the P,P-dimethyl groups of trimethyl PFA with bromotrimethylsilane (BTMS). 26,27 The amidation reaction was followed by 31 P NMR, which revealed replacement over several hours of the singlet resonance of 2 by a doublet due to CH-N-P coupling.…”