Synthesis of new 2',3'-dideoxy-6',6'-difluoro-3'-thionucleoside from gem-difluorohomoallyl alcohol.
[reaction: see text] 2',3'-Dideoxy-6',6'-difluoro-3'-thionucleoside 1b, an analogue of 3Tc that has high biological activities against HIV and HBV, has been synthesized from gem-difluorohomoallyl alcohol 3 in an efficient way. The key intermediate 4-amino-3,3-difluorotetrahydrothiophen-2-ylmethyl benzoate 15 was prepared from 2,2-difluoro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol 3 in 11 steps. The construction of pyrimidine ring with the amino group of compound 15 gave the target compound 1.
Wu
Yun-Yun
YY
Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Zhang
Xingang
X
Meng
Wei-Dong
WD
Qing
Feng-Ling
FL
D000605:Amino Alcohols / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D018360:Crystallography, X-Ray; D005466:Fluorocarbons / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
C502348:2',3'-dideoxy-6',6'-difluoro-3'-thionucleoside; D000605:Amino Alcohols; D000998:Antiviral Agents; D005466:Fluorocarbons; D020005:Propanols; D011743:Pyrimidines; D013872:Thionucleosides; C006463:allyl alcohol; C030986:pyrimidine