A simple and efficient synthesis of puromycin, 2,2'-anhydro-pyrimidine nucleosides, cytidines and 2',3'-anhydroadenosine from 3',5'-O-sulfinyl xylo-nucleosides.
Synthesis of antibiotics, puromycin and 3'-amino-3'-deoxy-N6,N6-dimethyladenosine 11 was achieved by utilizing the cyclic sulfite 6a of the xylo-3',5'-dihydroxy group as a new protective group. The key synthetic step is the deprotection of the sulfite moiety through the intramolecular cyclization of 2-alpha-carbamate 7. In a similar manner 2,2'-anhydro-pyrimidine nucleosides 15, ribo-cytidines 17 and 2',3'-anhydroadenosine 14 were prepared in high yields from the corresponding sulfites 4, 5, and 6b, respectively.
Takatsuki
Ken-ichi
K
Ichikawa Research Institute, Kobayashi Perfumery Co., Ltd., Ichikawa-City, Japan. vej05006@nifty.com
Ohgushi
Sumito
S
Kohmoto
Shigeo
S
Kishikawa
Keiki
K
Yamamoto
Makoto
M
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D003562:Cytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D003839:Deoxyadenosines / Q000138:chemical synthesis / Q000737:chemistry; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011691:Puromycin / Q000138:chemical synthesis* / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013456:Sulfur Acids / Q000737:chemistry
C513438:2',3'-anhydroadenosine; C513439:3'-amino-3'-deoxy-N(6),N(6)-dimethyladenosine; D003839:Deoxyadenosines; D009705:Nucleosides; D011741:Pyrimidine Nucleosides; D013456:Sulfur Acids; D011691:Puromycin; D003562:Cytidine; D000241:Adenosine