136090-71-6

Basic information

• Product Name: 1-<2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentafuranosyl>thymine 3'-(3-carboxypropanoate)
• CAS NO: 136090-71-6
• Molecular Weight: 644.678
• Mol File: 136090-71-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-<2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentafuranosyl>thymine 3'-(3-carboxypropanoate)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-<2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentafuranosyl>thymine 3'-(3-carboxypropanoate)(136090-71-6)
• EPA Substance Registry System: 1-<2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentafuranosyl>thymine 3'-(3-carboxypropanoate)(136090-71-6)

Safety Data

• Hazardous Substances Data: 136090-71-6(Hazardous Substances Data)

Upstream product

• 108-30-5 succinic acid anhydride 
• 40615-39-2 1-((2R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)- dione 
• 16053-52-4 threothymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 

Relevant articles and documents

1-(2'-Deoxy-β-D-xylofuranosyl)thymine Building Blocks for Solid-Phase Synthesis and Properties of Oligo(2'-Deoxyxylonucleotides)

1-(2'-Deoxy-β-D-threo-pentafuranosyl)thymine (= 1-(2'-deoxy-β-D-xylofuranosyl)thymine; xTd; 2) was converted into its phosphonate 3b as well as its 2-cyanoethyl phosphoramidite 3c.Both compounds were used for solid-phase synthesis of d (5), representing the first DNA fragment build up from 3'-5'-linked 2'-deoxy-β-D-xylonucleosides.Moreover, xTd was introduced into the innermost part of the self-complementary dodecamer d(G-T-A-A-xT-xT-C-T-A-C)2 (9).The CD spectrum of d (5) exhibits reversed Cotton effects compared to d(T12) (6; see Fig.1), implying a left-handed single strand.With d(A12) (7) it could be hybridized to form a propably left-handed double strand d(A12)*d (7*5) which was confirmed by melting experiments in combination with temperature-dependent CD spectroscopy.While 5 was hydrolyzed by snake-venom phosphodiesterase, it was resistant towards calf-spleen phosphodiesterase.The modified, self-complementary duplex 9 was hydrolyzed completely by snake-venom phosphodiesterase, at a twelvefold slower rate compared to unmodified 8; calf-spleen phosphodiesterase hydrolyzed 9 only partially.