First total synthesis of a naturally occurring nucleoside disulfide: 9-(5′-Deoxy-5′-thio-β-D-xylofuranosyl)adenine disulfide

被引：4

作者：

Ding, Hai Xin ^{[1
]}

Da, Ling Cui ^{[1
]}

Yang, Ru Chun ^{[1
]}

Cao, Ban Peng ^{[1
]}

Sun, Qi ^{[1
]}

Xiao, Qiang ^{[1
]}

机构：

[1] Jiangxi Sci & Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2012年 / 23卷 / 09期

关键词：

Naturally occurring nucleoside; Total synthesis; Vorbruggen glycosylation; Marine sponge; Nucleoside disulfide; NATURALLY-OCCURRING ANALOG; DORIS-VERRUCOSA;

D O I：

10.1016/j.cclet.2012.06.011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A naturally occurring nucleoside disulfide, 9-(5'-deoxy-5'-thio-beta-D-xylofuranosyl)adenine disulfide, was first synthesized from D-xylose over 7 steps in 20% overall yield. The key step involved Vorbruggen glycosylation of silylated N-6-benzoyladenine with xylose diacetate moiety. (C) 2012 Qiang Xiao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：996 / 998

页数：3

共 18 条

[1] First total synthesis of a naturally occurring nucleoside disulfide:9-(5'-Deoxy-5'-thio-β-D-xylofuranosyl)adenine disulfide
Hai Xin Ding
Chinese Chemical Letters, 2012, (09) : 996 - 998
[2] 9-(5′-Deoxy-5′-thio-β-D-xylofuranosyl)adenine Disulfide from the Southern Australian Marine Sponge Trachycladus laevispirulifer: the First Natural Occurrence of a Nucleoside Disulfide
Peng, Chongsheng
Gunaherath, G. M. Kamal B.
Piggott, Andrew M.
Khalil, Zeinab
Conte, Melissa
Capon, Robert J.
AUSTRALIAN JOURNAL OF CHEMISTRY, 2010, 63 (06) : 873 - 876
[3] HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC DETERMINATION OF A NATURALLY-OCCURRING XYLOSYL THIOETHER, 9-[5'-DEOXY-5'(METHYLTHIO)-BETA-D-XYLOFURANOSYL]ADENINE
PORCELLI, M
CACCIAPUOTI, G
OLIVA, A
ZAPPIA, V
JOURNAL OF CHROMATOGRAPHY, 1988, 440 : 151 - 155
[4] BIOSYNTHESIS AND METABOLISM OF 9-[5'-DEOXY-5'-(METHYLTHIO)-BETA-D-XYLOFURANOSYL]ADENINE, A NOVEL NATURAL ANALOG OF METHYLTHIOADENOSINE
PORCELLI, M
CACCIAPUOTI, G
CIMINO, G
GAVAGNIN, M
SODANO, G
ZAPPIA, V
BIOCHEMICAL JOURNAL, 1989, 263 (03) : 635 - 640
[5] SYNTHESIS OF 9-(5-DEOXY-BETA-D-ARABINOFURANOSYL)ADENINE
REIST, EJ
BARTUSKA, VJ
CALKINS, DF
GOODMAN, L
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (10): : 3401 - &
[6] Synthesis of 3′-deoxy-5′-S-ethyl-5′-thio-β-D-erythro-pentofuranosylthymine as potential antitumor agent
Al-Masoudi, NA
TETRAHEDRON LETTERS, 1999, 40 (26) : 4795 - 4796
[7] First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside
Sun, Jianyun
Dou, Yanhui
Ding, Haixin
Yang, Ruchun
Sun, Qi
Xiao, Qiang
MARINE DRUGS, 2012, 10 (04): : 881 - 889
[8] NUCLEOTIDES .31. MODIFIED OLIGOMERIC 2'-5' A ANALOGS - SYNTHESIS OF 2'-5' OLIGONUCLEOTIDES WITH 9-(3'-AZIDO-3'-DEOXY-BETA-D-XYLOFURANOSYL)ADENINE AND 9-(3'-AMINO-3'-DEOXY-BETA-D-XYLOFURANOSYL)ADENINE AS MODIFIED NUCLEOSIDES
HERDEWIJN, P
CHARUBALA, R
PFLEIDERER, W
HELVETICA CHIMICA ACTA, 1989, 72 (08) : 1729 - 1738
[9] SYNTHESIS OF 9-(5-AZIDO- AND 5-AMINO-5-DEOXY BETA-D-ARABINOFURANOSYL)ADENINE
STOUT, MG
ROBINS, RK
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (03) : 515 - &
[10] 5′-deoxy congeners of 9-(3-amido-3-deoxy-β-D-xylofuranosyl)-N6-cyclopentyladenine:: New adenosine A1 receptor antagonists
Van Calenbergh, S
Link, A
Fujikawa, S
Vanheusden, V
De Keukeleire, D
Ijzerman, AP
Herdewijn, P
CHEMISTRY OF NUCLEIC ACID COMPONENTS, 1999, 2 : 273 - 276

← 1 2 →