3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N6-benzyladenosine | 862490-65-1

• 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: 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N6-benzyladenosine
• CAS: 862490-65-1
• 化学式: C₂₉H₄₅N₅O₅Si₂
• 分子量: 599.878
• InChiKey: VWKNSOSDKXPZPI-CTDWIVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112.78
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N6-benzyladenosine 在 甲烷磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 [[(1R,3R,3aR,8aR)-3-(6-Benzylamino-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-2,4,6,8-tetraoxa-5,7-disila-azulen-1-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester
  参考文献：
  名称：

  o-Nitrobenzenesulfonamides in Nucleoside Synthesis:  Efficient 5‘-Aziridination of Adenosine

  摘要：

  5'-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-L-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford "bumped" cofactor mimics compatible with "hole"-bearing mutant proteins.

  DOI：

  10.1021/jo050205w
• 作为产物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 6-苄基腺苷 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 8.17h， 以80%的产率得到3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N6-benzyladenosine
  参考文献：
  名称：

  o-Nitrobenzenesulfonamides in Nucleoside Synthesis:  Efficient 5‘-Aziridination of Adenosine

  摘要：

  5'-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-L-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford "bumped" cofactor mimics compatible with "hole"-bearing mutant proteins.

  DOI：

  10.1021/jo050205w

文献信息

• An improved procedure for the acetalisation of alcoholic hydroxyl functions
  作者：H. C. P. F. Roelen、G. J. Ligtvoet、G. A. van der Marel、J. H. van Boom

  DOI：10.1002/recl.19871061008

  日期：——

  Acetalisation of 3′,5′-di-O-acetyluridine in DMF with 4,4-dimethoxytetrahydro-4H-pyran and 4,4-dimethoxytetrahydro-4H-1-thiopyran in the presence of trimethylsilyl chloride (TMSiCl) afforded, after removal of the acetyl groups, 2′-O-(4-methoxytetrahydropyranyl)-uridine and its sulfur analogue, respectively. It was also established that a 3′,5′-O-(tetraisopropyldisiloxane-1,3-diyl) protected ribonucleoside

  去除后，在存在三甲基甲硅烷基氯（TMSiCl）的情况下，将3'，5'-二-O-乙酰尿苷在DMF中与4,4-二甲氧基四氢-4H-吡喃和4,4-二甲氧基四氢-4H-1-硫吡喃缩醛化。的乙酰基分别为2′-O-（4-甲氧基四氢吡喃基）-尿苷及其硫类似物。还确定了使用TMSiCl促进的缩醛化方法将3'，5'-O-（四异丙基二硅氧烷-1,3-二基）保护的核糖核苷快速异构化为相应的2'，3'-异构体。
• Synthesis of 2′-O-α-d-ribofuranosyladenosine, monomeric unit of poly(ADP–ribose)
  作者：Sergey N. Mikhailov、Irina V. Kulikova、Koen Nauwelaerts、Piet Herdewijn

  DOI：10.1016/j.tet.2008.01.028

  日期：2008.3

  The first chemical synthesis of 2′-O-α-d-ribofuranosyladenosine, monomeric unit of poly(ADP–ribose), has been achieved starting from 3′,5′-O-bis protected 9-(2-O-α-d-arabinofuranosyl-β-d-ribofuranosyl)-adenine. Configurational inversion of 2′-hydroxyl group of arabinose moiety was performed by oxidation–reduction sequence.

  2'-的第一化学合成ö -α-d-ribofuranosyladenosine，聚（ADP-核糖）的单体单元，已经实现了从3开始'，5'- ø -双保护的9-（2- Ò -α- d-阿拉伯呋喃糖基-β-d-呋喃核糖基）-腺嘌呤。阿拉伯糖部分的2'-羟基的构型转化是通过氧化还原序列进行的。