First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside.
4-Amino-7-(5'-deoxy-β-D-xylofuranosyl)-5-iodo-pyrrolo[2,3-d]pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from D-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrüggen glycosylation of 5-iodo-pyrrolo[2,3-d]pyrimidine with 5-deoxy-1,2-O-diacetyl-3-O-benzoyl-D-xylofuranose. Its absolute configuration was confirmed.
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China.
Jianyun
J
Sun
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China.
Yanhui
Y
Dou
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China.
Haixin
H
Ding
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China.
Ruchun
R
Yang
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China.
Qi
Q
Sun
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China.
Qiang
0000-0003-2812-7778
Q
Xiao
D000818:Animals; D059001:Aquatic Organisms / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D006031:Glycosylation; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D014561:Urochordata / Q000737:chemistry*; D014994:Xylose / Q000737:chemistry
D001688:Biological Products; D006847:Hydrocarbons, Iodinated; D009705:Nucleosides; D007455:Iodine; D014994:Xylose