1985
DOI: 10.1139/v85-580
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Discussion on 13C nuclear magnetic resonance spectra of nucleoside derivatives. Reflection of structural alterations on 13C chemical shifts

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Cited by 6 publications
(4 citation statements)
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“…K. Anzai previously reported the preparation of 11 from the N 3 ,5¢-cyclonucleoside derivative of adenosine. 28,29 The 13 C NMR data that we obtained is identical to Anzai's result, 29 which confirmed our strucutural assignments. Chlorination at the 5¢-position of isoguanosine (3) was accomplished by the procedure reported by F. Seela et al 26 The reaction of isoguanosine (3) with thionyl chloride afforded 5¢-chloro-5¢-deoxyguanosine (9).…”
Section: Resultssupporting
confidence: 89%
“…K. Anzai previously reported the preparation of 11 from the N 3 ,5¢-cyclonucleoside derivative of adenosine. 28,29 The 13 C NMR data that we obtained is identical to Anzai's result, 29 which confirmed our strucutural assignments. Chlorination at the 5¢-position of isoguanosine (3) was accomplished by the procedure reported by F. Seela et al 26 The reaction of isoguanosine (3) with thionyl chloride afforded 5¢-chloro-5¢-deoxyguanosine (9).…”
Section: Resultssupporting
confidence: 89%
“…Thus, these two fractions were subjected to silica gel column chromatography and HPLC to give 29 pure compounds, including a new compound ( 1 ). Twenty-eight known compounds were identified as (7 R ,8 R )- threo -guaiacylglycerol 8- O -4′-sinapyl ether 7- O -β- d -glucopyranoside ( 2 ), (±)-syringaresinol ( 3 ), (±)-3′,3′′-bisdemethylpinoresinol ( 4 ), isoamericanol A ( 5 ), princepin ( 6 ), (−)-dehydrodiconiferyl alcohol 4- O -β- d -glucopyranoside ( 7 ), (±)-8,8′-dimethoxy-1- O -(β- d -glucopyranosyl) secoisolariciresinol ( 8 ), spionoside B ( 9 ), tachioside ( 10 ), koaburaside ( 11 ), 4-hydroxy-2,6-dimethoxyphenol 1- O -β- d -glucopyranoside, leonuriside ( 12 ), adenosine ( 13 ), tamarixetin 3- O -β- d -galactoside, americanol A, isoprincepin, (−)-5,5′-dimethoxy-4- O -(β- d -glucopyranosyl) lariciresinol, alangilignoside B, alangilignoside C, alangilignoside D, (−)-lariciresinol 4- O -β- d -glucopyranoside, 3α- O -β- d -glucopyranosyl lyoniresinol, icariside B 1 , roseoside, isotachioside, vanilloloside, 4-hydroxy-3-methoxyphenyl 1- O -β- d -xylopyranosyl-(1→6)-β- d -glucopyranoside, alangionoside C, and 4-(hydroxymethyl)-2,6-dimethoxyphenyl 1- O -β- d -glucopyranoside, respectively, by comparison of their spectroscopic data (especially NMR) and optical rotation with the reported values in the literature.…”
Section: Resultsmentioning
confidence: 99%
“…Fraction 7 [1.4 g: eluted with chloroform−MeOH−water (7:13:8)] was subjected to semipreparative HPLC [column: Tosoh, TSKgel ODS-100 V, 2 × 25 cm; solvent: acetonitrile−water (5:95); detector: 205 nm] to give 1 (2 mg; t R 34 min) and 4-hydroxy-3-methoxyphenyl 1- O -β- d -xylopyranosyl-(1→6)-β- d -glucopyranoside (2 mg; t R 32 min). All known compounds were identified by comparison with published data. …”
Section: Methodsmentioning
confidence: 99%
“…c ) Same numbering as for 14 -16. Assignments based on a HSQC spectrum and on comparison with data in[40].…”
mentioning
confidence: 99%