2',3'-O-isopropylideneadenosine 5'-aldehyde | 18210-77-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3'-O-isopropylideneadenosine 5'-aldehyde
• 英文别名: 2',3'-O-isopropylideneadenosine-5'-aldehyde；O^2'_,O3'-isopropylidene-5'-oxo-5'-deoxy-adenosine；1-(6-amino-purin-9-yl)-O²,O³-isopropylidene-β-D-ribo-1-deoxy-pentodiald-1,4-ose；5'-Desoxy-5'-oxo-2',3'-isopropyliden-adenosin, 2',3'-O-Isopropyliden-adenosin-5'-carbaldehyd；(3aR,4R,6S,6aS)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carbaldehyde
• CAS: 18210-77-0
• 化学式: C₁₃H₁₅N₅O₄
• 分子量: 305.293
• InChiKey: ZONZSERWDRIYJR-WOUKDFQISA-N

物化性质

• 沸点：
  562.7±60.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2',3'-O-isopropylideneadenosine 5'-aldehyde 在 sodium tetrahydroborate 、 lithium chloride 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 96.0h， 生成 9-(5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-heptofuranosyl)adenine
  参考文献：
  名称：

  Matsuda, Akira; Ueda, Tohru, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 4, p. 1573 - 1578

  摘要：

  DOI：
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯乙酸 为溶剂， 生成 2',3'-O-isopropylideneadenosine 5'-aldehyde
  参考文献：
  名称：

  锗基脱磺酰化反应在含锗核苷类似物合成中的应用

  摘要：

  用三丁基或三苯基锗烷 (AIBN/甲苯/Δ) 处理受保护的 (E)-5'-脱氧-5'-[(对甲苯磺酰基)亚甲基]尿苷和腺苷衍生物，产生自由基介导的锗基脱磺酰化，得到 5' -(三丁基-或三苯基锗基)亚甲基-5'-脱氧尿苷和腺苷衍生物作为单一 (E)-异构体。用 Ph3GeH 对 2'-脱氧-2'-[(苯基磺酰基)亚甲基]尿苷进行类似处理，得到相应的乙烯基三苯基锗烷产物。(E)-5'-(三丁基germyl)methylene-5'-deoxy 核苷与 N-iodosuccinimide 或 N-bromosuccinimide 的立体选择性卤代甲酰化提供 Wittig 型 (E)-5'-deoxy-5'-(halomethylene) 核苷定量，而 5'-deoxy-5'-(triphenylgermyl) 亚甲基对应物没有观察到卤化。

  DOI：

  10.1080/15257770903054340

文献信息

• Studies directed toward the total synthesis of sinefungin. I. Synthesis of 4-(5'-deoxyuridin-5'-yl)-4-nitrobutyronitrile, 4-(5'-deoxyadenosin-5'-yl)-4-nitrobutyramide and closely related nucleosides.
  作者：YOSHIHISA MIZUNO、KIYOMI TSUCHIDA、HAJIME TAMPO

  DOI：10.1248/cpb.32.2915

  日期：——

  S-Adenosylhomocysteine analogues, 1-(5, 6-dideoxy-6-nitro-β-D-ribo-hexofuranosyl) uracil (7a), 9-(5, 6-dideoxy-6-nitro-β-D-ribo-hexofuranosyl) adenine (7b), 4-(5'-deoxyuridin-5'-yl)-4-nitrobutyronitrile (15) and 4-(5'-deoxyadenosin-5'-yl)-4-nitrobutyramide (20) were synthesized as potential inhibitors of S-adenosylmethionine (SAM)-dependent methyltransferases and S-adenosylhomocysteine hydrolases. The chemistry developed for the preparation of these compounds should be useful in the total synthesis of the nucleoside antibiotics sinefungin and A9145C, which are potent inhibitors of certain SAM-dependent methyltransferases.

  S-腺苷同型半胱氨酸类似物，1-(5, 6-脱氧-6-硝基-β-D-戊糖-己糖苷)尿嘧啶（7a）、9-(5, 6-脱氧-6-硝基-β-D-戊糖-己糖苷)腺嘌呤（7b）、4-(5'-脱氧尿苷-5'-基)-4-硝基丁腈（15）和4-(5'-脱氧腺苷-5'-基)-4-硝基丁酰胺（20）被合成作为S-腺苷甲硫氨酸（SAM）依赖性甲基转移酶和S-腺苷同型半胱氨酸水解酶的潜在抑制剂。为这些化合物的合成所开发的化学方法应对核苷抗生素Sinefungin和A9145C的全合成有帮助，后者是某些SAM依赖性甲基转移酶的强效抑制剂。
• Nucleic acid related compounds. 63. Synthesis of 5′-deoxy-5′-methyleneadenosine and related Wittig-extended nucleosides
  作者：Stanislaw F. Wnuk、Morris J. Robins

  DOI：10.1139/v91-051

  日期：1991.2.1

  Treatment of the purified 5′-aldehyde (2a) (derived from 6-N-benzoyl-2′,3′-O-isopropylideneadenosine (1a)) with methylenetriphenylphosphorane and successive deprotection with ammonia and acid gave 9-(5,6-dideoxy-β-D-ribo-hex-5-enofuranosyl)adenine (5′-deoxy-5′-methyleneadenosine) (4). Oxidation of 1a or 2′,3′-O-isopropylideneadenosine (1b) and treatment of the crude 5′-aldehydes (2a or 2b) with (p-toluenesulfonylmethylene)triphenylphosphorane gave high yields of the 5′-deoxy-5′-tosylmethylene derivatives (5a or 5b). Removal of the tosyl group from 5b to give 3b was effected with tributylstannyllithium, but sulfone cleavage by the usual reductive methods failed. Reduction and deprotection of 5a or 5b gave 9-[5,6-dideoxy-6-(p-toluenesulfonyl)-β-D-ribo-hexofuranosyl]adenine (6b). Isomerization of the vinyl tosyl (5b) to a 4′,5′-unsaturated allylic tosyl derivative (7) occurred under cleavage conditions and in solutions of aqueous or organic bases. Key words: adenosine, 5′-deoxyadenosine, 5′-methylene-5′-deoxyadenosine, nucleosides.

  经过纯化的5'-醛(2a)(来源于6-N-苯甲酰基-2',3'-O-异丙基脱氧腺苷(1a))与三苯基膦甲烷反应，然后用氨水和酸进行连续脱保护，得到9-(5,6-二脱氧-β-D-核糖-己-5-烯基呋喃核苷)腺嘌呤(5'-脱氧-5'-亚甲基腺苷)(4)。氧化1a或2',3'-O-异丙基腺苷(1b)，然后用(p-甲苯磺酰亚甲基)三苯基膦烷处理粗的5'-醛(2a或2b)，得到5'-脱氧-5'-对甲苯磺酰亚甲基衍生物(5a或5b)的高产率。用三丁基锡基锂去除5b中的对甲苯磺酰基，但通常还原方法下的磺酰基裂解失败。还原和脱保护5a或5b得到9-[5,6-二脱氧-6-(对甲苯磺酰基)-β-D-核糖-己呋喃核苷]腺嘌呤(6b)。乙烯基对甲苯磺酰基(5b)在裂解条件下或水溶液或有机碱溶液中发生异构化，形成4',5'-不饱和联苯基对甲苯磺酰基衍生物(7)。关键词：腺苷，5'-脱氧腺苷，5'-亚甲基-5'-脱氧腺苷，核苷。
• Hollmann, Juergen; Schlimme, Eckhard, Liebigs Annalen der Chemie, 1984, # 1, p. 98 - 107
  作者：Hollmann, Juergen、Schlimme, Eckhard

  DOI：——

  日期：——
• Stereocontrolled Synthesis of Diene and Enyne Sugar-Modified Nucleosides and Their Interaction with<i>S</i>-Adenosyl-L-homocysteine Hydrolase
  作者：Stanislaw F. Wnuk、Pablo R. Sacasa、Leigh N. Crain、Elzbieta Lewandowska、Jinsong Zhang、Ronald T. Borchardt

  DOI：10.1081/ncn-120022634

  日期：2003.10

  Conjugated diene 5-7 and enyne 8 analogs derived from adenosine and uridine were synthesized employing Pd-catalyzed cross-coupling reactions.
• WNUK, STANISLAW F.;ROBINS, MORRIS J., CAN. J. CHEM., 69,(1991) N, C. 334-338
  作者：WNUK, STANISLAW F.、ROBINS, MORRIS J.

  DOI：——

  日期：——