[(3aR,5R,6S,6aR)-5-[(1R)-1,2-二羟基乙基]-2,2-二甲基-3a,5,6,6a-四氢呋喃并[4,5-d][1,3]二氧杂环戊烯-6-基]丁酸酯 | 125161-47-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: [(3aR,5R,6S,6aR)-5-[(1R)-1,2-二羟基乙基]-2,2-二甲基-3a,5,6,6a-四氢呋喃并[4,5-d][1,3]二氧杂环戊烯-6-基]丁酸酯
• 英文名称: 3-O-Butanoyl-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: Monobut 3；Monoacetone glucose 3-butyrate；[(3aR,5R,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] butanoate
• CAS: 125161-47-9
• 化学式: C₁₃H₂₂O₇
• 分子量: 290.313
• InChiKey: WFVFQUPBGWFLMB-DVYMNCLGSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6S,6aR)-5-[(1R)-1,2-二羟基乙基]-2,2-二甲基-3a,5,6,6a-四氢呋喃并[4,5-d][1,3]二氧杂环戊烯-6-基]丁酸酯 生成 [(2R)-2-[(3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] butanoate
  参考文献：
  名称：

  PIERI, FRANCOIS;RONCO, GINO;SEGARD, EMILE;VILLA, PIERRE

  摘要：

  DOI：
• 作为产物：
  描述：

  O³-butyryl-O¹,O²;O⁵,O⁶-diisopropylidene-α-D-glucofuranose 在 溶剂黄146 作用下， 生成 [(3aR,5R,6S,6aR)-5-[(1R)-1,2-二羟基乙基]-2,2-二甲基-3a,5,6,6a-四氢呋喃并[4,5-d][1,3]二氧杂环戊烯-6-基]丁酸酯
  参考文献：
  名称：

  Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives

  摘要：

  In this paper we report the synthesis of twelve 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives and the results obtained on their effects in inducing erythroid differentiation of human leukemic K562 cells. The data obtained demonstrate that two of the newly synthetized compounds are able to induce erythroid differentiation of K562 cells. In addition, these same compounds potentiate K562 erythroid differentiation induced by cytosine arabinoside, retinoic acid and mithramycin. Inducers of erythroid differentiation stimulating fetal gamma-globin synthesis could be considered for possible use in the experimental therapy of hematological diseases associated with a failure in the expression of adult beta-globin genes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00547-8

文献信息

• Glucidic esters of branched carboxylic acids capable of inducing erythroid cellular differentiation
  申请人：ASSOCIAZIONE VENETA PER LA LOTTA ALLA TALASSEMIA

  公开号：EP1004590A2

  公开（公告）日：2000-05-31

  The present invention provides compounds which are esters of a carbohydrate, constituted by a carbohydrate unit or a glycoside derived therefrom, having at least one alcohol group esterified with a branched chain carboxylic acid and having the remaining alcohol groups in part protected with a protector group, such as an isopropylidene group, and partly in the form of free hydroxyls. These carbohydrate esters being provided with a significant biological activity as erythroid cellular differentiation inducers can be utilised for the preparation of a medicament for the therapeutic treatment of β-talaxemia or tumours.

  本发明提供的化合物是一种碳水化合物的酯类，由碳水化合物单元或由其衍生的糖苷构成，具有至少一个醇基与支链羧酸酯化，并且其余的醇基部分被保护为保护基团，例如异丙基亚甲基基团，部分以自由羟基的形式存在。这些碳水化合物酯类具有显著的生物活性，可以诱导红细胞分化，可用于制备治疗β-地中海贫血或肿瘤的药物。
• Goueth, Pierre Y.; Gogalis, Pascalis; Bikanga, Raphael, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 2, p. 249 - 272
  作者：Goueth, Pierre Y.、Gogalis, Pascalis、Bikanga, Raphael、Gode, Paul、Postel, Denis、et al.

  DOI：——

  日期：——
• PIERI, FRANCOIS;RONCO, GINO;SEGARD, EMILE;VILLA, PIERRE
  作者：PIERI, FRANCOIS、RONCO, GINO、SEGARD, EMILE、VILLA, PIERRE

  DOI：——

  日期：——
• ESTERS DU D-MANNOSE OU DU XYLITOL ET LEUR UTILISATION COMME MEDICAMENTS
  申请人：L'ASSOCIAZIONE DI VOLONTARIATO "PRO LA FONDAZIONE FUTURO SENZA THALASSEMIA"

  公开号：EP0773949B1

  公开（公告）日：1999-11-10
• US5830872A
  申请人：——

  公开号：US5830872A

  公开（公告）日：1998-11-03