(3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopentafuran-2-one | 56487-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopentafuran-2-one
• 英文别名: (3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopenta[b]furan-2-one；[(3aR,4S,5R,6aS)-4-(methoxymethyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] acetate
• CAS: 56487-71-9
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: PMXCABOKYNXFFJ-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopentafuran-2-one 在 吡啶 、 二氯乙酸 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 四丁基氟化铵 、 zinc trifluoromethanesulfonate 、 二异丁基氢化铝 、 dimsyl sodium 、 potassium carbonate 、 sodium iodide 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 反应 29.5h， 生成 ((6a'R,7'S,9a'S,Z)-7'-formyl-5-methyl-3',6',6a',7',9',9a'-hexahydrodispiro[[1,3]dioxane-2,2'-cyclopenta[b]oxocine-8',2''-[1,3]dithiolan]-5-yl)methyl benzoate
  参考文献：
  名称：

  Total synthesis of the major human urinary metabolite of prostaglandin D2, a key diagnostic indicator

  摘要：

  DOI：

  10.1021/ja00344a047
• 作为产物：
  描述：

  Acetic acid (3aR,4S,5S,6S,6aR)-6-bromo-4-methoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以20.9 mg的产率得到(3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopentafuran-2-one
  参考文献：
  名称：

  2-吡喃酮和乙烯基硒化物的催化对映选择性逆电子需求 Diels-Alder 反应

  摘要：

  我们报告了缺电子 2-吡喃酮与各种苯基乙烯基硒化物在手性双（恶唑啉）/Cu(OTf) 2络合物催化下的不对称逆电子需求 Diels-Alder 反应。通过使用侧臂修饰的手性双（恶唑啉）配体，以良好至优异的产率（高达 99%）和对映选择性（高达98% ee) 在温和条件下。基于这一策略，完成了科里内酯的高度简洁的对映选择性合成。

  DOI：

  10.1055/a-1990-5276

文献信息

• From carbohydrates to carbocycles. 2. A free radical route to Corey lactone and other prostanoid intermediates
  作者：T. V. RajanBabu

  DOI：10.1021/jo00254a020

  日期：1988.9
• RAJANBABU, T. V., J. ORG. CHEM., 53,(1988) N 19, C. 4522-4530
  作者：RAJANBABU, T. V.

  DOI：——

  日期：——
• Methods
  申请人：Sattentau James Quentin

  公开号：US20070110759A1

  公开（公告）日：2007-05-17

  The presence of aldehydic groups on proteins and lipoproteins is associated with various pathological conditions such as atherosclerosis, diabetes and alcoholic liver disease. Respiratory syncytial virus (RSV) is a major cause of severe respiratory disease in infants and the elderly. RSV vaccine research has been impeded because a formalin-inactivated vaccine used in the 1960s predisposed infants to enhanced disease following subsequent natural infection. The molecular basis for the vaccine-induced hypersensitivity has not, however, been elucidated. We show here that addition of reactive carbonyl groups to ovalbumin (OVA) by treatment with glycolaldehyde or formaldehyde increases the protein's immunogenicity in mice, and biases the immune response towards a Th2-type response. The increased immunogenicity and the Th2-type response can both be abrogated by reductive elimination of the reactive carbonyl groups. We demonstrate that RSV inactivated by formaldehyde (FI-RSV), following a protocol used previously to prepare the vaccine, contains reactive carbonyl groups. Using a well-established model of FI-RSV vaccine-induced pathology, immunisation of mice with FI-RSV and subsequent challenge of the mice with live RSV induced Th2-type responses, lung eosinophilia and weight loss that were abrogated by reductive elimination of the reactive carbonyl groups. We thus propose that the addition of reactive carbonyl groups to RSV during inactivation is the major mechanism that drives the Th2-immune response and associated pathology. Moreover, we suggest that the addition of reactive carbonyl groups to other antigens, including vaccines, may be responsible for other hypersensitive and allergic reactions described in the literature.
• KEY INTERMEDIATE FOR SYNTHESIS OF PROSTAGLANDIN COMPOUND AND PREPARATION METHOD THEREOF
  申请人：SHENZHEN CATALYS TECHNOLOGY CO., LTD

  公开号：US20220281797A1

  公开（公告）日：2022-09-08

  The present invention relates to the technical field of organic chemical engineering, and in particular to a key intermediate for synthesizing prostaglandin compounds and a preparation method therefor. When applied to the synthesis of prostaglandin compounds, the process flow is simplified, the yield and product purity are improved, the production costs are reduced, and the industrial application is easy.