1',2',3',4',5'-penta-O-acetyl-1'-C-[(1R)-2-nitrocyclohexa-2,4-dienyl]-D-manno-pentitol | 171036-87-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1',2',3',4',5'-penta-O-acetyl-1'-C-[(1R)-2-nitrocyclohexa-2,4-dienyl]-D-manno-pentitol
• 英文别名: [(2R,3R,4R,5R)-2,3,4,5-tetraacetyloxy-5-[(1R)-2-nitrocyclohexa-2,4-dien-1-yl]pentyl] acetate
• CAS: 171036-87-6
• 化学式: C₂₁H₂₇NO₁₂
• 分子量: 485.445
• InChiKey: BEPFYUSFPYARKJ-GHRYLNIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1',2',3',4',5'-penta-O-acetyl-1'-C-[(1R)-2-nitrocyclohexa-2,4-dienyl]-D-manno-pentitol 在 sodium tetrahydroborate 、 sodium periodate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 97.25h， 生成
  参考文献：
  名称：

  Enantioselective synthesis of 1-nitrotricyclo[5,2,2,02,6]undeca-3,8-dienes via tandem consecutive asymmetric Diels–Alder reaction–Cope rearrangement

  摘要：

  The 1-glyco-2-nitrocyclohexa-2,4-dienes 1a and 5a react with cyclopentadiene to yield, almost exclusively, the 10-glyco-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes 4a and 8a. Formation of these products is explained as the result of a tandem consecutive asymmetric Diels-Alder reaction-Cope rearrangement. Periodate oxidation of deprotected sugar side-chains, followed by sodium borohydride reduction yielded enantiomerically pure 10-formyl- and 10-hydroxymethyl-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes. Structures have been determined by X-ray crystallographic and spectroscopic analyses, and chemical correlation. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00627-7
• 作为产物：
  描述：

  1'-C-<(1R,5R,6S)-5-acetoxy-6-nitrocyclohex-3-enyl>-1',2',3',4',5'-penta-O-acetyl-D-manno-pentitol 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以35%的产率得到1',2',3',4',5'-penta-O-acetyl-1'-C-[(1R)-2-nitrocyclohexa-2,4-dienyl]-D-manno-pentitol
  参考文献：
  名称：

  Serrano, Jose A.; Caceres, Luis E.; Roman, Emilio, Journal of the Chemical Society. Perkin transactions I, 1995, # 14, p. 1863 - 1872

  摘要：

  DOI：

文献信息

• Studies on the reactivity of (pentitol-1-yl)nitrocyclohexadienes with acetyl chloride in methanol
  作者：M. Baños、E. Román、J.A. Serrano

  DOI：10.1016/s0957-4166(03)00155-1

  日期：2003.5

  (Pentitol-1-yl)nitrocyclohexadienes with pentaacetylated D-galacto and D-manno sugar side-chains react in different ways when they are subjected to transesterification with acetyl chloride in methanol. Although both processes should commence with a deacetylation, subsequent intramolecular nucleophilic attack from the resulting hydroxyl groups on electrophilic carbons on the cyclohexadiene ring was dependant on the nature of the sugar side-chain, as well as on the configuration at the stereogenic carbon of the cyclohexadiene ring. Thus, D-manno nitrocyclohexadiene led to a complex mixture from which we could either isolate or identify products with dioxatricyclodecane dimethyl ketal, benzofuran, chromane-3,4-diol, bicyclic or tricyclic oximes, nitrobenzene, and nitrocyclohexenol structures. In contrast, D-galacto nitrocyclohexadiene led exclusively to a bicyclic oxime. (C) 2003 Elsevier Science Ltd. All rights reserved.