(5R)-1-O-benzyl-2-deoxy-3,4-O-(1-methylethylidene)-5-C-phenyl-D-erythro-pentitol | 1138239-06-1

• 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: (5R)-1-O-benzyl-2-deoxy-3,4-O-(1-methylethylidene)-5-C-phenyl-D-erythro-pentitol
• 英文别名: (R)-[(4R,5S)-2,2-dimethyl-5-(2-phenylmethoxyethyl)-1,3-dioxolan-4-yl]-phenylmethanol
• CAS: 1138239-06-1
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: UCDHYYIANKQWNS-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (5R)-1-O-benzyl-2-deoxy-3,4-O-(1-methylethylidene)-5-C-phenyl-D-erythro-pentitol 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到(5R)-1-O-benzyl-5-O-[(tert-butyl)(dimethyl)silyl]-2-deoxy-3,4-O-(1-methylethylidene)-5-C-phenyl-D-erythro-pentitol
  参考文献：
  名称：

  First stereoselective total synthesis of Goniothalesdiol A

  摘要：

  The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre was fixed by intramolecular oxy-Michael addition. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.01.050
• 作为产物：
  描述：

  [(4S,5S)-2,2-dimethyl-5-(2-phenylmethoxyethyl)-1,3-dioxolan-4-yl]-phenylmethanone 在 zinc(II) tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以85%的产率得到(5R)-1-O-benzyl-2-deoxy-3,4-O-(1-methylethylidene)-5-C-phenyl-D-erythro-pentitol
  参考文献：
  名称：

  Chiron方法立体选择性全合成鸟油醇A

  摘要：

  使用D-核糖作为手性前体，可以完成立体式合成鼠李素A（一种二羟基化的四氢吡喃化合物）的立体控制。涉及的关键步骤是芳基格氏反应，立体选择性烷氧基指导的酮还原以及分子内氧迈克尔的加成。

  DOI：

  10.1002/hlca.200900342

文献信息

• Stereoselective Total Synthesis of Goniothalesdiol A via Chiron Approach
  作者：Jhillu S. Yadav、Ragam Nageshwar Rao、Ragam Somaiah、Valaboju Harikrishna、Basi V. Subba Reddy

  DOI：10.1002/hlca.200900342

  日期：——

  The stereocontrolled synthesis of goniothalesdiol A, a dihydroxylated tetrahydropyran compound, has been accomplished using D‐ribose as chiral precursor. The key steps involved are aryl Grignard reaction, stereoselective alkoxy‐directed keto reduction, and intramolecular oxy‐Michael addition.

  使用D-核糖作为手性前体，可以完成立体式合成鼠李素A（一种二羟基化的四氢吡喃化合物）的立体控制。涉及的关键步骤是芳基格氏反应，立体选择性烷氧基指导的酮还原以及分子内氧迈克尔的加成。
• First stereoselective total synthesis of Goniothalesdiol A
  作者：J.S. Yadav、N. Rami Reddy、V. Harikrishna、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2009.01.050

  日期：2009.3

  The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre was fixed by intramolecular oxy-Michael addition. (C) 2009 Published by Elsevier Ltd.