(3R,4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxy-dihydrofuran-2-one | 157453-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxy-dihydrofuran-2-one
• 英文别名: 5-O-tert-butyldimethylsilyl-D-ribono-1,4-lactone
• CAS: 157453-65-1
• 化学式: C₁₁H₂₂O₅Si
• 分子量: 262.378
• InChiKey: VEYHFQXUICKQJA-IWSPIJDZSA-N

物化性质

• 沸点：
  325.1±11.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxy-dihydrofuran-2-one 在 镍 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 27.5h， 生成 (5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one
  参考文献：
  名称：

  合成3-C-烷基（或3-C-苯基-）2，3-二脱氧-D-赤-戊基-1，4-内酯的合成路线：合成2（3H）-呋喃酮的中间体。

  摘要：

  一系列3-C-烷基-（和3-C-苯基-）2，3-二脱氧-D-赤-戊基-1，4-内酯，这些化合物在合成修饰的核苷和抗生素糖中很重要，由D-核糖内酯合成。通过经由5-O-保护的D-核糖内酯进行的途径，合成了5-O-保护的2,3-二脱氧-D-甘油-戊-2-enono-1,4-内酯，并与R2CuLi或络合物反应用PhSCu（RMgBr）n分别得到3-C-烷基或3-C-苯基化合物。提供了O-保护的中间体的制备以及有机金属试剂的选择的细节。

  DOI：

  10.1016/0008-6215(94)80066-9
• 作为产物：
  描述：

  (3AR,6R,6AR)-6-((苄氧基)甲基)-2,2-二甲基二氢呋喃并[3,4-D][1 在 咪唑 、 乙醇 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (3R,4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxy-dihydrofuran-2-one
  参考文献：
  名称：

  High-Yielding Diastereoselective syn -Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O -Protected Analogues

  摘要：

  A diastereoselective chemoenzymatic synthetic pathway to D‐(+)‐ribono‐1,4‐lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose‐based levoglucosenone (LGO). This route involves a sustainable Baeyer‐Villiger oxidation of LGO to produce enantiopure (S)‐γ‐hydroxymethyl‐α,β‐butenolide (HBO) that is further functionalized with various protecting groups to provide 5‐O‐protected γ‐hydroxymethyl‐α,β‐butenolides. The latter then undergo a diastereoselective and high‐yielding syn‐dihydroxylation of the α,β‐unsaturated lactone moiety followed by a deprotection step to give D‐(+)‐ribono‐1,4‐lactone. Through this 4‐step synthetic route from LGO, D‐(+)‐ribono‐1,4‐lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5‐O‐tert‐butyldimethylsilyl‐, 5‐O‐tert‐butyldiphenylsilyl‐ as well as 5‐O‐benzyl‐ribono‐1,4‐lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.

  DOI：

  10.1002/ejoc.201801780

文献信息

• Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors
  作者：Dong Jin Hwang、Sun Nam Kim、Jung Hoon Choi、Yong Sup Lee

  DOI：10.1016/s0968-0896(01)00013-x

  日期：2001.6

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. Such integration is essential for the production of progeny viruses, and therefore therapeutic agents that can inhibit this process should be effective anti-HIV agents. We have previously reported the inhibitory activity of dicaffeoylglucosides against HIV IN. In the present study, we have synthesized and tested dicaffeoyl or digalloyl compounds joined through a five-membered heterocyclic ring as HIV IN inhibitors to explore the SARs of this family of compounds. The starting heterocyclic diols were prepared from L-tartaric acid, diethyl L-tartarate or D-(+)-ribonic gamma -lactone. We found that the HIV IN inhibitory activities of dicaffeoyl derivatives were comparable to that of L-chicoric acid (IC50 = 24.9 muM). On the other hand, digalloyl derivatives were more potent than L-chicoric acid with IC50 Values of 4.7-15.6 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.