[(2R,3S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,3-bis(phenylmethoxy)propyl] 4-methylbenzenesulfonate | 436148-62-8

• 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-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,3-bis(phenylmethoxy)propyl] 4-methylbenzenesulfonate
• CAS: 436148-62-8
• 化学式: C₂₉H₃₄O₇S
• 分子量: 526.651
• InChiKey: WAGOJEYJZWWTFN-FCEKVYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,3-bis(phenylmethoxy)propyl] 4-methylbenzenesulfonate 在 水 、 sodium hydride 、 碳酸氢钠 、 copper(II) sulfate 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 12.0h， 生成 (3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(3,4,5-trimethoxy-phenyl)-butan-1-one
  参考文献：
  名称：

  Umpolung Strategy for the Synthesis of 2-Deoxy-C-aryl Glycosides:  A Serendipitous, Efficient Route for C-Furanoside Analogues

  摘要：

  [GRAPHICS]2-Deoxy-C-aryl glycosides are potential synthetic targets as they form a very vital moiety of several biologically active natural products. This paper describes a synthetic route using an umpolung strategy, which has not been explored till date. Our synthetic endeavor led to a versatile intermediate aryl ketone 10, which has paved the way for two important classes of C-glycosides, viz, C-alkyl furanosides 12 and methyl 2-deoxy-C-aryl pyranosides 14.

  DOI：

  10.1021/ol025794w
• 作为产物：
  描述：

  3,4-di-O-benzyloxy-5,6-O-isopropylidene-D-mannitol 在 lead(IV) acetate 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 [(2R,3S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,3-bis(phenylmethoxy)propyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  从d-甘露糖醇合成5-羟烷基丁烷-4-油化物的有效策略：（-）-多卡他霉素的全合成

  摘要：

  已经描述了从d-甘露糖醇合成5-羟基烷基丁烷-4-醇化物的一般方法。该方法已成功用于抗肿瘤天然产物（-）-muricatacin的全合成。

  DOI：

  10.1016/s0040-4039(02)00375-1

文献信息

• An efficient strategy for the synthesis of 5-hydroxyalkylbutan-4-olides from d-mannitol: total synthesis of (−)-muricatacin
  作者：M Chandrasekhar、Kusum L Chandra、Vinod K Singh

  DOI：10.1016/s0040-4039(02)00375-1

  日期：2002.4

  A general approach towards the synthesis of 5-hydroxyalkylbutan-4-olides from d-mannitol has been described. The approach has successfully been used for the total synthesis of (−)-muricatacin, an anti-tumor natural product.

  已经描述了从d-甘露糖醇合成5-羟基烷基丁烷-4-醇化物的一般方法。该方法已成功用于抗肿瘤天然产物（-）-muricatacin的全合成。
• Total Synthesis of (−)- and (+)-Lentiginosine
  作者：Kusum L. Chandra、M. Chandrasekhar、Vinod K. Singh

  DOI：10.1021/jo025677e

  日期：2002.6.1

  Total synthesis of (-)-lentiginosine was achieved from D-mannitol using highly stereoselective reactions. Similarly, (+)-lentiginosine was synthesized from L-tartaric acid.

  使用高度立体选择性反应，由D-甘露糖醇可实现（-）-龙胆草碱的全合成。类似地，由L-酒石酸合成（+）-龙胆苷。
• Umpolung Strategy for the Synthesis of 2-Deoxy-<i>C</i>-aryl Glycosides:  A Serendipitous, Efficient Route for <i>C</i>-Furanoside Analogues
  作者：S. Vijayasaradhi、Indrapal Singh Aidhen

  DOI：10.1021/ol025794w

  日期：2002.5.1

  [GRAPHICS]2-Deoxy-C-aryl glycosides are potential synthetic targets as they form a very vital moiety of several biologically active natural products. This paper describes a synthetic route using an umpolung strategy, which has not been explored till date. Our synthetic endeavor led to a versatile intermediate aryl ketone 10, which has paved the way for two important classes of C-glycosides, viz, C-alkyl furanosides 12 and methyl 2-deoxy-C-aryl pyranosides 14.