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The Resource Synthesis and antiviral evaluation of some 3'-Carboxymethyl-3'-deoxyadenosine derivatives, by Houguang Shi

Synthesis and antiviral evaluation of some 3'-Carboxymethyl-3'-deoxyadenosine derivatives, by Houguang Shi

Label
Synthesis and antiviral evaluation of some 3'-Carboxymethyl-3'-deoxyadenosine derivatives
Title
Synthesis and antiviral evaluation of some 3'-Carboxymethyl-3'-deoxyadenosine derivatives
Statement of responsibility
by Houguang Shi
Creator
Subject
Genre
Language
eng
Summary
3'-Carboxymethyl-3'-deoxyadenosine derivatives were prepared from 2'-O-TBDMS-3'-deoxy-3'-[(ethoxycarbonyl)methyl]adenosine (1) via simple and efficient procedures. Conversion of 1 to 5'-azido-2'-O-TBDMS-3', 5'-dideoxy -3'-[(ethoxycarbonyl) methyl] adenosine (4) was accomplished via a novel one-pot method employing 5'-activation (TosCl) followed by efficient nucleophilic displacement with tetramethylguanidinium azide. Compound 4 was converted to a 5'-[(N-methylcarbamoyl)amino] derivative (5) via one-pot reduction/acylation employing H2/Pd-C followed by treatment with p-nitrophenyl N-methylcarbamate. The latter step of this two-step process required an efficient source of p-nitrophenyl N-methylcarbamate, thus a highly efficient new method for preparing p-nitrophenyl N-alkylcarbamate was developed. N6-phenylcarbamoyl groups were introduced by treatment with phenylisocyanate, and an efficient new method for lactonization of 2'-O-TBDMS-3'-deoxy-3'-[(ethoxycarbonyl)methyl]adenosines to give corresponding 2', 3'-lactones was also developed. Target compounds were evaluated for anti-HIV and anti-HIV integrase activities, but were not active at the concentrations tested
Cataloging source
UPB
Degree
M.S.
Dissertation year
2007
Granting institution
Brigham Young University. Dept. of Chemistry and Biochemistry
Illustrations
illustrations
Index
no index present
Literary form
non fiction
Nature of contents
  • bibliography
  • theses
Label
Synthesis and antiviral evaluation of some 3'-Carboxymethyl-3'-deoxyadenosine derivatives, by Houguang Shi
Link
http://hdl.lib.byu.edu/1877/etd1940
Instantiates
Publication
Bibliography note
Includes bibliographical references (p. 60-63)
Carrier category
volume
Carrier MARC source
rdacarrier
Content category
text
Content type MARC source
rdacontent
Dimensions
28 cm.
Extent
x, 63 p.
Media category
unmediated
Media MARC source
rdamedia
Other physical details
ill.
System control number
  • UtOrBLW
  • (OCoLC)ocn376895622
Label
Synthesis and antiviral evaluation of some 3'-Carboxymethyl-3'-deoxyadenosine derivatives, by Houguang Shi
Link
http://hdl.lib.byu.edu/1877/etd1940
Publication
Bibliography note
Includes bibliographical references (p. 60-63)
Carrier category
volume
Carrier MARC source
rdacarrier
Content category
text
Content type MARC source
rdacontent
Dimensions
28 cm.
Extent
x, 63 p.
Media category
unmediated
Media MARC source
rdamedia
Other physical details
ill.
System control number
  • UtOrBLW
  • (OCoLC)ocn376895622

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