102977-57-1

Basic information

• Product Name: [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl [(2R,3S,4R,5R)-5-(4-carbamoyl-1,3-thiazol-2-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl methanediylbis[hydrogen (phosphonate)] (non-preferred name)
• CAS NO: 102977-57-1
• Molecular Formula: C₂₀H₂₇N₇O₁₃P₂S
• Molecular Weight: 667.48
• Mol File: 102977-57-1.mol

Chemical Properties

• Boiling Point: 1124.9°C at 760 mmHg
• Flash Point: 634.1°C
• Density: 2.29g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.912
• CAS DataBase Reference: [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl [(2R,3S,4R,5R)-5-(4-carbamoyl-1,3-thiazol-2-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl methanediylbis[hydrogen (phosphonate)] (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl [(2R,3S,4R,5R)-5-(4-carbamoyl-1,3-thiazol-2-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl methanediylbis[hydrogen (phosphonate)] (non-preferred name)(102977-57-1)
• EPA Substance Registry System: [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl [(2R,3S,4R,5R)-5-(4-carbamoyl-1,3-thiazol-2-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl methanediylbis[hydrogen (phosphonate)] (non-preferred name)(102977-57-1)

Safety Data

• Hazardous Substances Data: 102977-57-1(Hazardous Substances Data)

Upstream product

• 60084-11-9 2-(2',3'-O-isopropylidene-β-D-ribofuranosyl)thiazole-4-carboxamide 
• 102977-56-0 adenosine 5'-(α,β-methylene)diphosphate 
• 3768-14-7 O^5'-(dihydroxyphosphorylmethyl-hydroxy-phosphinoyl)-adenosine 
• 188413-05-0 P¹,P²,P³,P⁴-bismethylene-P¹,P⁴-di(2',3'-O-isopropylideneadenosine) tetraphosphonate 

Relevant articles and documents

The practical synthesis of a methylenebisphosphonate analogue of benzamide adenine dinucleotide: Inhibition of human inosine monophosphate dehydrogenase (type I and II)

β-Methylene-BAD (8), a nonhydrolyzable analogue of benzamide adenine dinucleotide (BAD), was synthesized as potential inhibitor of human inosine monophosphate dehydrogenase (IMPDH). Treatment of 2',3'O- isopropylideneadenosine 5'-methylenebisphosphonate (15) with DCC afforded P1,P4-bis(2',3'-O-isopropylideneadenosine) 5'-P1,P2:P3,p4- dimethylenetetrakisphosphonate (17). This compound was further converted with DCC to an active intermediate 18 which upon reaction with 3.(2',3'-O- isopropylidene-β-D-ribofuranosyl)benzamide (19) gave, after hydrolysis and deisopropylidenation, the desired β-methylene-BAD (8) in'95% yield. In a similar manner, treatment of 18 with 2',3'-O-isopropylidenetiazofurin (21) followed by hydrolysis and aleprotection afforded β-methylene-TAD (5) in 91% yield. Compound 8 (IC50 = 0.665 μM) was found to be a 6-8 times less potent inhibitor of IMPDH than 5 (IC50 = 0.107 μM) and was almost equally potent against IMPDH type I and type II. Although TAD and β-methylene-TAD were bound by LADH with the same affinity, the binding affinity of 8 toward LADH (K(i) = 333 μM) was found to be 50-fold lower than that of the parent pyrophosphate 7 (K(i) = 6.3 μM).

Efficient synthesis of methylenebis(phosphonate) analogues of P1,P2-disubstituted pyrophosphates of biological interest. A novel plausible mechanism

Synthesis of novel nucleoside bicyclic trisanhydrides 7 in the reaction of nucleoside-5'-methylenebis(phosphonate)s (4) with DCC is described. They were obtained by P1,P3- and P2,P4-dehydration of initially form