(S)-3-hydroxybutyrolactone, benzyloxy methyl ether | 73991-96-5

• 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: (S)-3-hydroxybutyrolactone, benzyloxy methyl ether
• 英文别名: (S)-3-(benzyloxymethoxy)dihydrofuran-2-one；2(3H)-Furanone, dihydro-3-[(phenylmethoxy)methoxy]-, (S)-；(3S)-3-(phenylmethoxymethoxy)oxolan-2-one
• CAS: 73991-96-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: QDPKFXAXDKTNTM-NSHDSACASA-N

物化性质

• 沸点：
  368.6±37.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-hydroxybutyrolactone, benzyloxy methyl ether 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2,2-Dimethyl-propionic acid (S)-3-benzyloxymethoxy-4-oxo-pentyl ester
  参考文献：
  名称：

  First Asymmetric Total Syntheses of (−)-Subincanadines A and B, Skeletally Rearranged Pentacyclic Monoterpenoid Indole Alkaloids in Aspidosperma subincanum

  摘要：

  [GRAPHICS]We achieved the first asymmetric total syntheses of novel Aspidosperma indole alkaloids, (-)-subincanadines A and B, which involve an intramolecular diastereoselective Pictet-Spengler cyclization and an intramolecular Nozaki-Hiyama-Kishi reaction as key steps in the total syntheses.

  DOI：

  10.1021/ol061908i
• 作为产物：
  描述：

  苄基氯甲基醚 、 (S)-(-)-α-羟基-γ-丁内酯 在 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以79%的产率得到(S)-3-hydroxybutyrolactone, benzyloxy methyl ether
  参考文献：
  名称：

  亚胺中偏二价阴离子的立体化学。在（1 S，8a S）-1-羟基吲哚并咪唑的合成中的应用

  摘要：

  （1立体选择性路线小号，8α小号）-1- hydroxyindolizidine在本文报道了包含作为关键步骤的非对映选择性加入4-（苯磺酰基）丁酸（4-PSBA）的二价阴离子的手性α -苄氧基甲基亚胺。

  DOI：

  10.1016/0040-4020(95)00037-9

文献信息

• Stereochemistry of remote dianion addition to imines. Application to the synthesis of (1S, 8aS)-1-hydroxyindolizidine
  作者：Diana L.C. Green、James J. Kiddle、Charles M. Thompson

  DOI：10.1016/0040-4020(95)00037-9

  日期：1995.3

  A stereoselective route to (1S, 8aS)-1-hydroxyindolizidine is reported herein that incorporates as a pivotal step the diastereoselective addition of the dianion of 4-(phenylsulfonyl)butanoic acid (4-PSBA) to a chiral α-benzyloxymethyl imine.

  （1立体选择性路线小号，8α小号）-1- hydroxyindolizidine在本文报道了包含作为关键步骤的非对映选择性加入4-（苯磺酰基）丁酸（4-PSBA）的二价阴离子的手性α -苄氧基甲基亚胺。
• New methods and reagents in organic synthesis. 63. Synthesis of mugineic acid through direct C-acylation using diphenyl phosphorazidate (DPPA)
  作者：Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1021/jo00376a102

  日期：1986.12
• Synthesis of the polyether antibiotic monensin. 2. Preparation of intermediates
  作者：David B. Collum、John H. McDonald、W. Clark Still

  DOI：10.1021/ja00526a074

  日期：1980.3
• Synthesis of (-)-slaframine and related indolizidines
  作者：William H. Pearson、Stephen C. Bergmeier、John P. Williams

  DOI：10.1021/jo00040a045

  日期：1992.7

  An enantioselective synthesis of the indolizidine alkaloid (-)-slaframine 1 is reported. Reductive double cyclization of the azido epoxy tosylate 48 afforded the indolizidine 52, which was converted to (-)-slaframine in two steps. The cyclization substrate 48 was prepared in optically pure form from L-glutamic acid. A similar sequence starting with the epoxide 49 allowed the synthesis of (-)-1,8a-diepislaframine 56. Other routes to slaframine were investigated, often using an intramolecular cycloaddition of an azide with an alkene as a key step. Although these routes did not produce slaframine, they illustrated novel and efficient methods for the assembly of the indolizidine skeleton. Cyclization of the azidodiene 20 afforded the indolizidine 21 in one step as a single diastereomer, presumably a result of a chairlike transition state in the initial dipolar cycloaddition. Desulfurization and deprotection produced (-)-8a-epidesacetoxyslaframine 27. Cyclopropylimine rearrangement of 30 gave the indolizidine 31, which was also converted into (-)-8a-epidesacetoxyslaframine 27. Dipolar cycloaddition of 38 gave the 1-pyrroline 39, which was converted to the indolizidine 40 in one operation using Evans' double alkylation of the 1-metalloenamine derivative of 40. Attempted oxidation of 40 to the ketone 41 was unsuccessful, precluding a reductive amination approach to slaframine.
• An enantioselective synthesis of (−)-slaframine
  作者：Jong-Ryoo Choi、Shin Han、Jin K. Cha

  DOI：10.1016/0040-4039(91)80195-c

  日期：1991.11

  An enantioselective synthesis of (-)-slaframine (1) has been accomplished by an intramolecular azide [2 + 3] dipolar cycloaddition starting from the readily available aldehyde 12.