cyclohexyl 2-deoxy-α-D-glucopyranoside | 63069-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 2-deoxy-α-D-glucopyranoside
• 英文别名: 1-O-Cyclohexyl-2-deoxy-α-D-glucopyranosid；(2R,3S,4R,6S)-6-cyclohexyloxy-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 63069-87-4
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: ADKDGHRVIQAIDR-WYUUTHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose 在 sodium tetrahydroborate 、 4 A molecular sieve 、 Amberlite IRN-78 OH^(1-) form 、 三苯基膦氢溴酸盐 作用下， 以 甲醇 、 苯 为溶剂， 反应 5.0h， 生成 cyclohexyl 2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of α‐2‐Deoxyglycosides by Acid‐Mediated Conjugate Addition

  摘要：

  A new method for the synthesis of alpha-2-deoxyglycosides from hex-1-en-3-uloses is reported. Several acids were surveyed for their ability to mediate the conjugate addition of cyclohexanol to a glucal derived alpha,beta-unsaturated ketone. Although several acids successfully afforded the alpha-2-deoxy-3-uloside as a single anomer, Ph3P (.) HBr in benzene afforded the highest yield of product. These conditions were then applied to other alcohol nucleophiles, and it was found that nonsterically hindered alcohols readily undergo conjugate addition. Finally, the stereoselectivity of reduction of the resulting alpha-2-deoxy-3-uloside was determined for several hydride-reducing agents.

  DOI：

  10.1081/car-200059931

文献信息

• Enzymatic synthesis of alkyl α-2-deoxyglucosides by alkyl alcohol resistant α-glucosidase from Aspergillus niger
  作者：Young-Min Kim、Masayuki Okuyama、Haruhide Mori、Hiroyuki Nakai、Wataru Saburi、Seiya Chiba、Atsuo Kimura

  DOI：10.1016/j.tetasy.2004.11.046

  日期：2005.1

  Aspergillus niger alpha-glucosidase (ANGase) was used for an efficient syntheses of alkyl alpha-D-2-deoxyglucosides (A2DGs) and for regioselectivity studies of alkoxy-hydro additions Of D-glucal in the presence of alkyl alcohols. ANGase showed a high stability with respect to the high concentration of alkyl alcohols. The reaction conditions were optimized for pH, temperature, alkyl alcohol concentration, and D-glucal concentration. On the basis of MS and NMR analyses, A2DGs were confirmed to have only an alpha-2deoxyglucosidic bond and the two-dimensional NMR (HMBC) spectra showed to be made up of 2-deoxyglucosyl and alkyl moieties. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of α‐2‐Deoxyglycosides by Acid‐Mediated Conjugate Addition
  作者：Brent Mann、Daniel Pitts、Jennifer Koviach

  DOI：10.1081/car-200059931

  日期：2005.3

  A new method for the synthesis of alpha-2-deoxyglycosides from hex-1-en-3-uloses is reported. Several acids were surveyed for their ability to mediate the conjugate addition of cyclohexanol to a glucal derived alpha,beta-unsaturated ketone. Although several acids successfully afforded the alpha-2-deoxy-3-uloside as a single anomer, Ph3P (.) HBr in benzene afforded the highest yield of product. These conditions were then applied to other alcohol nucleophiles, and it was found that nonsterically hindered alcohols readily undergo conjugate addition. Finally, the stereoselectivity of reduction of the resulting alpha-2-deoxy-3-uloside was determined for several hydride-reducing agents.