(3aR,3bR,6R,7R,7aR,8aR)-7-azido-2,2-dimethyl-hexahydro-1,3,4,8-tetraoxa-cyclopenta[a]inden-6-ol | 864941-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (3aR,3bR,6R,7R,7aR,8aR)-7-azido-2,2-dimethyl-hexahydro-1,3,4,8-tetraoxa-cyclopenta[a]inden-6-ol
• 英文别名: (2R,3R,3bR,6R,7R,7aR)-7-azido-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-6-ol；(1R,2R,6R,8R,9R,10R)-9-azido-4,4-dimethyl-3,5,7,12-tetraoxatricyclo[6.4.0.02,6]dodecan-10-ol
• CAS: 864941-68-4
• 化学式: C₁₀H₁₅N₃O₅
• 分子量: 257.246
• InChiKey: LMBAAQFQCAEXKX-IXTJBZSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,3bR,6R,7R,7aR,8aR)-7-azido-2,2-dimethyl-hexahydro-1,3,4,8-tetraoxa-cyclopenta[a]inden-6-ol 在 sodium tetrahydroborate 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 6.0h， 生成 (2R,3R,3bR,6S,7R,7aR)-7-azido-6-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran
  参考文献：
  名称：

  A Scalable Synthesis of 1-Cytosinyl-N-malayamycin A:  A Potent Fungicide

  摘要：

  A stereocontrolled synthesis of 1-cytosinyl-N-malayamycin A, an N-analogue of the naturally occurring malayamycin A with fungicidal activity, is reported. The approach was designed to rely solely on substrate control for introduction of the required stereochemistry, avoiding the use of chiral reagents or auxiliaries. Formation of the N-nucleoside was achieved through the activation of a thioglycoside, proceeding via sulfonium and thionium intermediates. Ring closure metathesis was used to build the bicyclic perhydrofuropyran heterocycle.

  DOI：

  10.1021/op0600299
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 Grubbs catalyst first generation 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 水 、 四丁基碘化铵 、 溶剂黄146 、 三乙胺 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二醇甲醚 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 36.17h， 生成 (3aR,3bR,6R,7R,7aR,8aR)-7-azido-2,2-dimethyl-hexahydro-1,3,4,8-tetraoxa-cyclopenta[a]inden-6-ol
  参考文献：
  名称：

  A Scalable Synthesis of 1-Cytosinyl-N-malayamycin A:  A Potent Fungicide

  摘要：

  A stereocontrolled synthesis of 1-cytosinyl-N-malayamycin A, an N-analogue of the naturally occurring malayamycin A with fungicidal activity, is reported. The approach was designed to rely solely on substrate control for introduction of the required stereochemistry, avoiding the use of chiral reagents or auxiliaries. Formation of the N-nucleoside was achieved through the activation of a thioglycoside, proceeding via sulfonium and thionium intermediates. Ring closure metathesis was used to build the bicyclic perhydrofuropyran heterocycle.

  DOI：

  10.1021/op0600299

文献信息

• Total Synthesis of <i>N</i>-Malayamycin A and Related Bicyclic Purine and Pyrimidine Nucleosides
  作者：Stephen Hanessian、Guobin Huang、Caroline Chenel、Roger Machaalani、Olivier Loiseleur

  DOI：10.1021/jo050727b

  日期：2005.8.1

  synthesis of bicyclic perhydrofuropyran nucleosides as N-analogues of the naturally occurring malayamycin A. Formation of the N-nucleosides relied on the activation of thioglycosides, proceeding via sulfonium intermediates. Ring closure metathesis was used in two approaches to build the bicyclic dioxa heterocycle. Another approach relied on the use of a sugar precursor and cyclization to the bicyclic thioglycoside

  方法双环perhydrofuropyran核苷的全合成被描述为Ñ -analogues所述的天然存在的malayamycin A.形成的Ñ核苷依靠硫代糖苷的激活，经由锍中间体进行。闭环复分解用于两种方法来构建双环二氧杂环杂环。另一种方法依赖于糖前体的使用和环化成双环硫代糖苷。
• A Scalable Synthesis of 1-Cytosinyl-<i>N</i>-malayamycin A:  A Potent Fungicide
  作者：Olivier Loiseleur、Hermann Schneider、Guobin Huang、Roger Machaalani、Patrice Sellès、Patrick Crowley、Stephen Hanessian

  DOI：10.1021/op0600299

  日期：2006.5.1

  A stereocontrolled synthesis of 1-cytosinyl-N-malayamycin A, an N-analogue of the naturally occurring malayamycin A with fungicidal activity, is reported. The approach was designed to rely solely on substrate control for introduction of the required stereochemistry, avoiding the use of chiral reagents or auxiliaries. Formation of the N-nucleoside was achieved through the activation of a thioglycoside, proceeding via sulfonium and thionium intermediates. Ring closure metathesis was used to build the bicyclic perhydrofuropyran heterocycle.