(2R,3S)-3-(benzyloxy)-1,2-epoxybutane | 114185-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-3-(benzyloxy)-1,2-epoxybutane
• 英文别名: (2R)-2-[(1S)-1-phenylmethoxyethyl]oxirane
• CAS: 114185-04-5
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: HZMPMAWIQIUION-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(benzyloxy)-1,2-epoxybutane 在 盐酸 、 dilithium tetrabromonickelate(II) 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 1-<<(3S)-(benzyloxy)-1-bromo-(2R)-butoxy>methyl>thymine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1‘,2‘-Seconucleo-5‘-phosphonates

  摘要：

  A series of 1',2'-seconucleophosphonate analogues were prepared containing adenine, cytosine, thymine, and uracil as the nucleobase. The synthetic methodology is efficient and uses chloromethyl ethers derived from the chirons diethyl (3S)-(benzyloxy)-(2R)-hydroxybutanephosphonate (1) and diethyl (3S),4-bis(benzyloxy)-(2R)-hydroxybutanephosphonate (2). Selected deblocked derivatives, i.e., two monoesters (13 and 14), four phosphonic acids (15-18), and one cyclic phosphonate (23), were screened for in vitro activity against certain RNA, adeno, and HIV viruses. All of them were found to be devoid of activity.

  DOI：

  10.1021/jm9506783
• 作为产物：
  描述：

  (2R,3S)-3-O-benzyl-1,2-O-isopropylidenebutane-1,2,3-triol 在 Amberlite IR-120 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 20.0h， 生成 (2R,3S)-3-(benzyloxy)-1,2-epoxybutane
  参考文献：
  名称：

  The chemistry of L-ascorbic and D-isoascorbic acids. 1. The preparation of chiral butanetriols and -tetrols

  摘要：

  DOI：

  10.1021/jo00246a037

文献信息

• Aplyronine A, a potent antitumor macrolide of marine origin, and the congeners aplyronines B and C: isolation, structures, and bioactivities
  作者：Makoto Ojika、Hideo Kigoshi、Yoshifumi Yoshida、Takeshi Ishigaki、Masanori Nisiwaki、Itaru Tsukada、Masayuki Arakawa、Hisao Ekimoto、Kiyoyuki Yamada

  DOI：10.1016/j.tet.2007.02.011

  日期：2007.4

  isolated from the sea hare Aplysia kurodai together with the congeners aplyronines B (3) and C (4). The absolute stereostructure of aplyronine A (2) was determined by the instrumental analysis (mainly NMR and MS) and the enantioselective synthesis of the fragments obtained from chemical degradation of aplyronine A (2). The structures of aplyronines B (3) and C (4) were also elucidated. Cytotoxicity and

  从海兔Aplysia kurodai中分离到了一种有效的抗肿瘤大环内酯-Aplyronine A（2），以及同类的aplyronines B（3）和C（4）。通过仪器分析（主要是NMR和MS）和对苯丙氨酸A（2）的化学降解获得的片段的对映选择性合成，确定了苯丙氨酸A（2）的绝对立体结构。还阐明了鸭绿素B（3）和C（4）的结构。肾上腺素A（2）的细胞毒性和抗肿瘤活性进行了评估。
• Absolute Stereochemistry of Aplyronine A, a Potent Antitumor Substance of Marine Origin
  作者：Makoto Ojika、Hideo Kigoshi、Takeshi Ishigaki、Itaru Tsukada、Takaya Tsuboi、Takeshi Ogawa、Kiyoyuki Yamada

  DOI：10.1021/ja00095a071

  日期：1994.8
• A general and facile synthesis of .beta.- and .gamma.-hydroxy phosphonates from epoxides
  作者：Zhengong Li、Saibaba Racha、Li Dan、Hussein El-Subbagh、Elie Abushanab

  DOI：10.1021/jo00073a043

  日期：1993.10

  A practical and facile method for the preparation of hydroxy phosphonate esters is described. Regiospecific ring opening of monosubstituted epoxides by phosphorus and carbon nucleophiles, derived from diethyl phosphite and methanephosphonates, in the presence of BF3.OEt2 furnishes the corresponding beta- and gamma-hydroxy phosphonates, respectively. Ketals, bromides, sulfonate esters, and carbamates (compounds 12, 13, 15, 16, and 18) are stable under the reaction conditions, but benzoate esters(14) behave differently. While they survive phosphite nucleophilicity, they are cleaved by phosphonates. Several chirons (2, 28a, 30b, and 31) for the synthesis of phosphonate isosteres of nucleotides and phospholipids are also described.
• ABUSHANAB, ELIE;VEMISHETTI, PURUSHOTHAM;LEIBY, ROBERT W.;SINGH, HARIBINSH+, J. ORG. CHEM., 53,(1988) N 11, 2598-2602
  作者：ABUSHANAB, ELIE、VEMISHETTI, PURUSHOTHAM、LEIBY, ROBERT W.、SINGH, HARIBINSH+

  DOI：——

  日期：——