Guanine Adenine H CHOH CH,OH NH2 H H H OH OH Guanosine Adenosine (鸟苷) (腺苷) Thymine Cytosine H CHOH CH,OH O H H OH OH H Cytidine Uridine (胞啶) (尿苷
N N N N NH2 O O O H3 C H Adenine Guanine Cytosine Thymine O CH2OH OH OH N N N N NH2 H H H H O CH2OH OH OH N N N N O H H H H H NH2 O CH2OH OH OH H H H H O CH2OH OH OH H H H H Adenosine (腺苷) Guanosine (鸟苷) Cytidine (胞啶) Uridine (尿苷)
253 LABORATORY SYNTHESIS OF NUCLEOSIDES AND NUCLEOTIDES One technique uses reaction that assemble the nucleoside from suitably activated and protected ribose derivatives and heterocyclic vase NHCOCH3 NHCOCH CH2OCOCH3 H n - y CH2OCOCH3N N H20-Adenosine OH OCOCH3 OCOCH3 Hgcl COCH COCH Another technique involves formation of the heterocyclic base on a protected ribosylamine derivative
25.3 LABORATORY SYNTHESIS OF NUCLEOSIDES AND NUCLEOTIDES One technique uses reaction that assemble the nucleoside from suitably activated and protected ribose derivatives and heterocyclic base. N N N N NHCOCH3 HgCl O CH2OCOCH3 OCOCH3 OCOCH3 H Cl + -HgCl 2 N N N N NHCOCH3 O CH2OCOCH3 OCOCH3 OCOCH3 OH - H2O Adenosine Another technique involves formation of the heterocyclic base on a protected ribosylamine derivative
O C6HsOCOH,C NH O H2 HC NH_(-2C2HsOH) hao Uridine OCOCkH CH C=O C6HsOCOH2C OCOC6H5 OCHs OC2H5 OCOC6H5 OCOC6H5 The third technique involves the synthesis of a nucleosides with a substituent in the heterocyclic ring that can be replaced with other NH, groups H CH,OH R H OHOH N
O C6H5OCOH2C OCOC6H5 OCOC6H5 NH2 + OH - H2O HC Uridine CH OC2H5 C NH O C O OC2H5 (-2C2H5OH) O C6H5OCOH2C OCOC6H5 OCOC6H5 N N O O H The third technique involves the synthesis of a nucleosides with a substituent in the heterocyclic ring that can be replaced with other groups. O CH2OH OH OH N N N N Cl H H H H NH3 H2 S Ni N N N N NH2 R N N N N S R H N N N N R R =