2-{(4R,6S)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxan-4-yl}ethanol | 171599-00-1

• 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: 2-{(4R,6S)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxan-4-yl}ethanol
• 英文别名: (3S,5S)-7-(Benzyloxy)-3,5-O-isopropylideneheptane-1,3,5-triol；2-[(4R,6S)-2,2-dimethyl-6-(2-phenylmethoxyethyl)-1,3-dioxan-4-yl]ethanol
• CAS: 171599-00-1
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: MRGFUDWELACNBW-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{(4R,6S)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxan-4-yl}ethanol 在 咪唑 、 2,6-二甲基吡啶 、 四氧化锇 、 碘 、 叔丁基锂 、 L-Selectride 、 戴斯-马丁氧化剂 、 N-甲基吗啉氧化物 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 9.78h， 生成
  参考文献：
  名称：

  Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B

  摘要：

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.

  DOI：

  10.1021/jo00129a019
• 作为产物：
  描述：

  (2S,4R)-2-(N-Benzylamino)-4-<oxy>-6-hepten-1-ol 在 盐酸 、 sodium hydroxide 、 四氧化锇 、 四丁基氯化铵 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 sodium sulfite 作用下， 以 甲醇 、 正己烷 、 氯仿 、 水 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 14.49h， 生成 2-{(4R,6S)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxan-4-yl}ethanol
  参考文献：
  名称：

  Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B

  摘要：

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.

  DOI：

  10.1021/jo00129a019

文献信息

• A novel strategy towards the atorvastatin lactone
  作者：Pramod Sawant、Martin E. Maier

  DOI：10.1016/j.tet.2010.10.028

  日期：2010.12

  We describe a novel strategy to the atorvastatin lactone based on a Paal–Knorr synthesis of pyrrole 24 by condensing diketone 23 with primary amine 22. The latter contains the syn-1,3-diol subunit and a benzyl ether function at the other end of the chain. This allowed for manipulations on the pyrrole ring via iodination at C2, metalation with t-BuLi and carboxylation. The obtained acid 26 could be

  我们通过将二酮23与伯胺22缩合，基于Paal-Knorr合成吡咯24来描述阿托伐他汀内酯的新策略。后者在链的另一端包含顺-1，3-二醇亚基和苄基醚官能团。这允许通过在C 2处碘化，用t- BuLi金属化和羧基化来对吡咯环进行操作。可以通过酰胺形成，脱苄基作用，氧化作用和内酯化作用将获得的酸26转化为阿托伐他汀内酯6。关键组成部分2-（（4 R，6 S）-6-（2-（苄氧基）乙基）-2,2-二甲基-1,3-二恶烷-4-基）乙胺（根据Krische，通过两个连续的不对称转移氢化羰基烯丙基化获得22）。
• A convergent preparation of the C1–C13 fragment of amphotericin B from a single chiral precursor
  作者：Carlo Bonini、Lucia Chiummiento、Angela Martuscelli、Licia Viggiani

  DOI：10.1016/j.tetlet.2004.01.035

  日期：2004.3

  short, highly efficient, stereoconvergent synthesis of the polyolic chain, C1–C13, of the macrolide antibiotic amphotericin B is described. The key features of the synthesis are the use of a single chiral precursor for the establishment of the stereogenic centres in a short synthetic sequence, and the final alkyl lithium addition to the appropriate aldehyde, which showed high diastereoselectivity for

  描述了大环内酯类抗生素两性霉素B的多元链C1-C13的短而高效的立体收敛合成。合成的关键特征是使用单一的手性前体以较短的合成顺序建立立体异构中心，最后烷基锂添加到适当的醛中，对第五种立体异构正确的立体化学显示出较高的非对映选择性。中心。
• Preparation of chiral 1,3 skipped anti- and syn-tetrols via highly enantioselective biocatalytic resolution
  作者：Carlo Bonini、Lucia Chiummiento、Maria Funicello

  DOI：10.1016/s0957-4166(01)00467-0

  日期：2001.10

  Biocatalytic resolution of the 7-benzyloxy-3,5-anti-dioxolan-1,3 5,7-tetrol and the 7-benzyloxy-3,5-syn-dioxolan-1,3,5,7-tetrol was found to be highly enantioselective leading to differently functionalized chiral tetrols with significantly high e.e. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B
  作者：Glenn J. McGarvey、Jeffrey A. Mathys、Kenneth J. Wilson、Kenneth R. Overly、Paul T. Buonora、P. Grant Spoors

  DOI：10.1021/jo00129a019

  日期：1995.12

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.