51600-11-4

Basic information

• Product Name: Adenosine, 5'-O-[(4-methoxyphenyl)diphenylmethyl]-
• CAS NO: 51600-11-4
• Molecular Formula: C30H29N5O5
• Molecular Weight: 539.591
• Mol File: 51600-11-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Adenosine, 5'-O-[(4-methoxyphenyl)diphenylmethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, 5'-O-[(4-methoxyphenyl)diphenylmethyl]-(51600-11-4)
• EPA Substance Registry System: Adenosine, 5'-O-[(4-methoxyphenyl)diphenylmethyl]-(51600-11-4)

Safety Data

• Hazardous Substances Data: 51600-11-4(Hazardous Substances Data)

Upstream product

• 14470-28-1 mono-4-methoxytrityl chloride 
• 58-61-7 adenosine 
• 66224-66-6 adenine 
• 127246-75-7 N⁶-benzoyl-2',3'-di-O-p-tolylsulphonyladenosine 
• 40601-49-8 2',3'-di-O-p-tolylsulphonyladenosine 
• 112141-39-6 5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 88121-73-7 N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 148144-77-8 5'-O-(monomethoxytrityl)-N⁶2'-O,3'-O-tris<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 127277-91-2 5'-O-monomethoxytrityl-2',3'-di-O-p-tolylsulphonyladenosine 
• 4546-55-8 N-benzoyladenosine 

Downstream Products

• 29886-19-9 2',3'-di-O-acetyladenosine 
• 1070898-19-9 5'-O-(4-monomethoxytrityl)-2'-O-(methoxycarbonyl)methyladenosine 
• 1070898-21-3 C₃₂H₃₂N₆O₆ 
• 131372-53-7 9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldiphenylsilyl)-3'-O-trifluoromethanesulfonyl-β-D-xylofuranosyl>adenine 
• 131372-48-0 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldiphenylsilyl)-3'-O-trifluoromethanesulfonyladenosine 
• 131372-47-9 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-O-(trifluoromethanesulfonyl)adenosine 
• 131372-52-6 9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-O-trifluoromethanesulfonyl-β-D-xylofuranosyl>adenine 
• 131372-51-5 9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl>adenine 
• 83373-09-5 9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>adenine 
• 131372-50-4 9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldiphenylsilyl)-3'-O-acetyl-β-D-xylofuranosyl>adenine 

Relevant articles and documents

Discovery of Leucyladenylate Sulfamates as Novel Leucyl-tRNA Synthetase (LRS)-Targeted Mammalian Target of Rapamycin Complex 1 (mTORC1) Inhibitors

Recent studies indicate that LRS may act as a leucine sensor for the mTORC1 pathway, potentially providing an alternative strategy to overcome rapamycin resistance in cancer treatments. In this study, we developed leucyladenylate sulfamate derivatives as LRS-targeted mTORC1 inhibitors. Compound 18 selectively inhibited LRS-mediated mTORC1 activation and exerted specific cytotoxicity against colon cancer cells with a hyperactive mTORC1, suggesting that 18 may offer a novel treatment option for human colorectal cancer.

Synthesis and stability of a 2′-O-[N-(aminoethyl)carbamoyl] methyladenosine-containing dinucleotide

Working towards the synthesis of 2′-O-[N-(aminoethyl)carbamoyl] methyl-modified di- and oligonucleotides, we have synthesised a protected 2′-O-[N-(aminoethyl)carbamoyl]methyl-modified adenosine where the modification is introduced in a convenient one-pot three-step procedure. The corresponding H-phosphonate building block was also synthesised, and from this intermediate, a 2′-O-[N-(aminoethyl)carbamoyl]methyl-containing dinucleotide could be made. We also performed studies on the chemical and enzymatic stability of this dinucleotide. The dinucleotide was subjected to different ammonolysis and other basic conditions, and HPLC analysis showed that the modification was intact to most conditions, but that there was some minor hydrolysis when NH3 (concd. aq.) was used at 55 °C. Under several other sets of conditions, including saturated NH3 in methanol, and ethylenediamine, the amide remained intact. Treatment of the dinucleotide with Phosphodiesterase I from Crotalus adamanteus venom and Phosphodiesterase II from bovine spleen showed that the N-(aminoethyl)carbamoylmethyl moiety gives the phosphodiester linkage substantial protection against enzymatic degradation; the phosphodiester was not degraded by PDE II at all after seven days. A 2′-O-[N-(aminoethyl)carbamoyl]methyl-modified adenosine and a corresponding dinucleotide were synthesised. Hydrolysis (1-2 %) was observed in concentrated aqueous NH3 at 55°C, but under several other sets of reaction conditions, the amide remained intact. The N-(aminoethyl) carbamoylmethyl moiety gave substantial protection against enzymatic degradation by nucleases from snake venom and bovine spleen. Copyright

REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE

The reaction of lithium triethylborohydride with the 2',3'-di-O-p-tolylsulphonyl derivatives of 9-β-D-ribofuranosyladenine, 9-β-D-arabinofuranosyladenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied.The reaction of 2',3'-di-O-p-tolylsulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine.This rearrangement reaction was used for the synthesis of 9-(3,5-dideoxy-β-D-threo-pentofuranosyl)adenine in one step from 2',3',5'-tri-O-p-tolylsulphonyladenosine in 58percent yield.The p-tolylsulphonyl group in the 2'-"up" configuration of unprotected adenine nucleosides was preferentially attacked by LiEt3BH giving S-O-bond scission.This was shown by the formation of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine from 2',3'-di-O-p-tolylsulphonyl-9-β-D-arabinofuranosyladenine and by the formation of 9-β-D-lyxofuranosyladenine from 2'-O-p-tolylsulphonyl-9-β-D-lyxofuranosyladenine with LiEt3BH. 9-β-D-Lyxofuranosyladenine was synthesized from 3',5'-di-O-benzoyl-9-β-D-xylofuranosyladenosine in 88percent yield using a triflate displacement reaction.