cyclohexyl 4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranosid-3-ulose | 862252-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranosid-3-ulose
• 英文别名: 1-cyclohexyl-4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranoside-3-ulose；[(2R,3R,6S)-3-acetyloxy-6-cyclohexyloxy-4-oxooxan-2-yl]methyl acetate
• CAS: 862252-86-6
• 化学式: C₁₆H₂₄O₇
• 分子量: 328.362
• InChiKey: YIDCJFRYROWFJG-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cyclohexyl 4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranosid-3-ulose 在 sodium tetrahydroborate 、 Amberlite IRN-78 OH^(1-) form 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (2R,3S,4S,6S)-6-Cyclohexyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol
  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
• 作为产物：
  描述：

  4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose 、 环己醇 在 4 A molecular sieve 、 三苯基膦氢溴酸盐 作用下， 以 苯 为溶剂， 以61%的产率得到cyclohexyl 4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranosid-3-ulose
  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

• Microwave-assisted stereoselective α-2-deoxyglycosylation of hex-1-en-3-uloses
  作者：Hui-Chang Lin、Hsu-Hsuan Wu、Zi-Ping Lin、Chih-Yuan Lin、Chun-Hung Lin、Kun-Lung Chen、Fung Fuh Wong

  DOI：10.1016/j.tetlet.2009.10.049

  日期：2009.12

  alpha-2-Deoxyglycosides were successfully synthesized by means of microwave-assisted glycosylation. Hex-1-en-3-uloses were treated with a catalytic amount of AlCl3 and various O-nucleophiles including alcohols and sugars under microwave conditions. The desired alpha-2-deoxy-ulosides products were obtained in good to excellent yields with high stereoselectivity (alpha/beta >= 88/12). Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.