(2R)-1,2-diacetoxy-3-(benzyloxy)propane | 17325-87-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2R)-1,2-diacetoxy-3-(benzyloxy)propane
• 英文别名: (R)-3-O-Benzyl-1,2-O-diacetylglycerol；(S)-3-benzyloxy-1,2-diacetoxypropane；[(2R)-2-acetyloxy-3-phenylmethoxypropyl] acetate
• CAS: 17325-87-0
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: PZJWZGWBDMSONK-CQSZACIVSA-N

物化性质

• 沸点：
  360.9±32.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (2R)-1,2-diacetoxy-3-(benzyloxy)propane 在 palladium on activated charcoal 、 四(三苯基膦)钯 copper(l) iodide 、 三正丁胺 、 mercury(II) diacetate 、 氢气 、 溴 、 正丁胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 Petrosyne Ia triacetate
  参考文献：
  名称：

  Structure and synthesis of petrosynes, new acetylenic enol ether glycerides from the Okinawan marine sponge of the genus Petrosia

  摘要：

  Acetylenic enol ether glycerides, 1 and 3, were found in the Okinawan marine sponge of the genus Petrosia. The plane structures of these glycerides were deduced from spectroscopic analysis. Their complete structures were established by enantioselective total synthesis of all possible stereoisomers using (R)-1-O-benzylglycerol and its (S)-enantiomer, prepared from D-mannitol and L-ascorbic acid, respectively, as chiral building blocks. The synthesis involves the palladium(O)-catalyzed coupling reaction of bromo enol ether 9 with enediyne 21 as a key step. It became evident from the synthesis that the natural product 1 consisted of a mixture of (7R,2'S)-24 (petrosyne Ia) and (7S,2S)-24 (petrosyne Ib), and the natural product 3 consisted of a mixture of (7R,2'S)-28 (petrosyne IIa) and (7S,2'S)-28 (petrosyne IIb).

  DOI：

  10.1021/jo00073a030
• 作为产物：
  描述：

  [(2S)-5,5,5-trifluoro-1-phenylmethoxypent-3-yn-2-yl] acetate 在 Lindlar catalyst 吡啶 、 sodium tetrahydroborate 、 二甲基硫 、 氢气 、 potassium carbonate 、 臭氧 作用下， 以 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2R)-1,2-diacetoxy-3-(benzyloxy)propane
  参考文献：
  名称：

  经由酯-烯醇酸酯[2,3] -Wittig和[3,3]-爱尔兰-克莱森重排的高立体选择性合成三氟甲基化化合物。

  摘要：

  γ-三氟甲基化的炔丙醇已通过有效的酶动力学拆分以光学纯的形式获得，然后转化为（E）-或（Z）-烯丙基醇。相应的[[γ-（三氟甲基）烯丙基]氧基]乙酸甲酯的[2,3] -Wittig重排提供了高产率的α-羟基-β-（三氟甲基）-γ-δ-不饱和羧酸甲酯。（Z）-底物的重排以高度立体选择性的方式进行，以通过完全手性转移在新产生的烯烃键上得到具有E构型的抗异构体。然而，（E）-底物显示出相对较低的立体选择性，导致合成产物和反产物混合。三氟甲基化的烯丙基醇也被转化为相应的α-甲氧基乙酸γ-（三氟甲基）烯丙基酯，并被评估为[3，3]-爱尔兰-克莱森重排的底物。（E）-底物被有效地转化为合成产物，而（Z）-底物表现出相对较低的立体选择性。两种互补方法为具有高度立体控制的高度官能化的含三氟甲基的分子提供了简便的途径。

  DOI：

  10.1021/jo961246i

文献信息

• Nucleophilic displacement reactions of the methanesulfonates of the 1-O-benzoyl-1,2-, -1,3-, and -1,4-glycols
  作者：Seiichi Takano、Michiyasu Hirama、Kazuhiko Seya、Kunio Ogasawara

  DOI：10.1016/s0040-4039(00)88309-4

  日期：——

  Nucleophilic displacement reactions of the methanesulfonates (a–c) of the 1-O-benzoyl-1,2-, -1,3-, and -1,4-glycols (a–c) with potassium acetate in boiling acetic anhydride have been examined. Both benzoyloxy-group participation pathway (path ) and SN2 displacement pathway (path ) have been involved in the 1,2-(a)- and 1,3-(b)-substrates to give a mixture of the primary (a,b) and the secondary (a,b)

  1- O-苯甲酰基-1,2-，-1,3-和-1,4-乙二醇（a-c）的甲磺酸盐（a -c）与乙酸钾在沸腾乙酸酐中的亲核取代反应具有经过检查。1,2-（a）-和1,3-（b）-底物均涉及苯甲酰氧基基团参与途径（path ）和S N 2置换途径（path ），从而形成主要（a ，b）和具有完全手性反转的仲（a，b）乙酸盐。另一方面，在1，4-底物（c）中仅涉及S N 2置换途径（路径），以得到具有手性反转的仲乙酸酯（c）。
• Lipase-catalyzed enantiomer selective hydrolysis of 1,2-diol diacetates
  作者：László Poppe、Lajos Novák、Mária Kajtár-Peredy、Csaba Szántay

  DOI：10.1016/s0957-4166(00)80071-3

  日期：1993.10

  Enantiomer selective hydrolysis of racemic 1,2-diol diacetates (rac-2a-h) was investigated by using the inexpensive commercial porcine pancreatic lipase. The hydrolysis proceeds with variable regioselectivity but with moderate to good enantioselectively yielding a mixture of isomeric monoacetates (3a-h and 4a-h) and unchanged diacetate enantiomers (2a-h). Evidence was found that both monoacetates (3a-h and 4a-h) are formed with the same sense of enantiomer selectivity.
• Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG)
  作者：Giuseppe Guanti、Luca Banfi、Andrea Basso、Elisabetta Bevilacqua、Laura Bondanza、Renata Riva

  DOI：10.1016/j.tetasy.2004.07.040

  日期：2004.9

  A new efficient chemoenzymatic methodology for the production of 3-O-benzyl-sn-glycerol and 1,2-O-dipalmitoyl-sn-glycerol has been developed. It starts from racemic 1-O-benzylglycerol and is based on the sequential enzymatic acylation-Mitsunobu inversion-enzymatic hydrolysis, which has been performed without isolation of the intermediates. In this way a 70-75% yield of 3-O-benzyl-sn-glycerol with 94-96% ee has been obtained. (C) 2004 Published by Elsevier Ltd.
• Regio- and enantioselective esterifications of polyoxygenated compounds catalyzed by lipases
  作者：Bernardo Herradón、Sénida Cueto、Anabel Morcuende、Serafín Valverde

  DOI：10.1016/s0957-4166(00)80123-8

  日期：1993.5

  The lipase catalyzed esterifications of derivatives of propane-1,2,3-triol and butane-1,2,4-triol in organic solvents have been studied. The influence of several factors (lipase source, organic solvent, additives and structural variations in die substrates) on the selectivity have been investigated. Good levels of regio- and enantioselectivity have been achieved, providing practical methods for the synthesis of these chiral building blocks.
• TAKANO, SEIICHI;HIRAMA, MICHIYASU;SEYA, KAZUHIKO;OGASAWARA, KUNIO, TETRAHEDRON LETT., 1983, 24, N 39, 4233-4236
  作者：TAKANO, SEIICHI、HIRAMA, MICHIYASU、SEYA, KAZUHIKO、OGASAWARA, KUNIO

  DOI：——

  日期：——