3,4-Di-O-benzyl-2,6-dideoxy-L-gluconolactone | 148914-38-9

• 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: 3,4-Di-O-benzyl-2,6-dideoxy-L-gluconolactone
• 英文别名: 3,4-di-O-benzyl-2,6-dideoxy-L-arabino-hexono-1,5-lactone；(4S,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)oxan-2-one
• CAS: 148914-38-9
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: UUTDIZXSJVPFFD-QSFXBCCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  3,4-Di-O-benzyl-2,6-dideoxy-L-gluconolactone 在 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3S,4S)-3,4-bis(benzyloxy)-3,4-dihydro-2-methyl-6-phenyl-2H-pyran
  参考文献：
  名称：

  Preparation of 2-deoxy-.beta.-C-arylglycosides and C-arylglycals from carbohydrate lactones

  摘要：

  DOI：

  10.1021/jo00063a051
• 作为产物：
  描述：

  3,4-di-O-benzyl-L-rhamnal 在 mercury(II) diacetate 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 3,4-Di-O-benzyl-2,6-dideoxy-L-gluconolactone
  参考文献：
  名称：

  Preparation of C-arylglycals via Suzuki–Miyaura cross-coupling of dihydropyranylphosphates

  摘要：

  The preparation of C-arylglycals has been accomplished by employing the Suzuki-Miyaura cross-coupling reaction of dihydropyranylphosphates with arylboronate esters. The reaction is tolerant of both electron-donating (EDG) and electron-withdrawing (EWG) groups on the aromatic ring and affords the corresponding C-arylglycals in good to excellent yields (68-97%). Additionally, the ketene acetal phosphate derived from 6-deoxy-3,4-di-O-benzyl-L-rhamnal also couples efficiently to yield C-arylglycals in excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.031

文献信息

• Facile synthesis of C-aryl glycals from sugar-derived lactones
  作者：Hui Li、Kristen Procko、Stephen F. Martin

  DOI：10.1016/j.tetlet.2006.02.150

  日期：2006.5

  A general entry to C(I) aryl-substituted glycals from the corresponding sugar lactones is described. This approach features one-pot access to aryl glycals. A variety of aryllithium reagents can be used and the method is compatible with various 2-deoxysugar lactones. (c) 2006 Elsevier Ltd. All rights reserved.
• Zagar, Cyrill; Scharf, Hans-Dieter, Liebigs Annalen der Chemie, 1993, # 4, p. 447 - 450
  作者：Zagar, Cyrill、Scharf, Hans-Dieter

  DOI：——

  日期：——
• Preparation of C-arylglycals via Suzuki–Miyaura cross-coupling of dihydropyranylphosphates
  作者：Michelle R. Leidy、J. Mason Hoffman、Rongson Pongdee

  DOI：10.1016/j.tetlet.2013.10.031

  日期：2013.12

  The preparation of C-arylglycals has been accomplished by employing the Suzuki-Miyaura cross-coupling reaction of dihydropyranylphosphates with arylboronate esters. The reaction is tolerant of both electron-donating (EDG) and electron-withdrawing (EWG) groups on the aromatic ring and affords the corresponding C-arylglycals in good to excellent yields (68-97%). Additionally, the ketene acetal phosphate derived from 6-deoxy-3,4-di-O-benzyl-L-rhamnal also couples efficiently to yield C-arylglycals in excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Preparation of 2-deoxy-.beta.-C-arylglycosides and C-arylglycals from carbohydrate lactones
  作者：Vincent A. Boyd、Brian E. Drake、Gary A. Sulikowski

  DOI：10.1021/jo00063a051

  日期：1993.5