1-S-α-toluenyl-2-deoxy-4,6-di-O-p-methoxybenzyl-α-D-erythro-hexopyranos-3-ulose | 1423038-38-3

• 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: 1-S-α-toluenyl-2-deoxy-4,6-di-O-p-methoxybenzyl-α-D-erythro-hexopyranos-3-ulose
• 英文别名: (2R,3R,6R)-6-benzylsulfanyl-3-[(4-methoxyphenyl)methoxy]-2-[(4-methoxyphenyl)methoxymethyl]oxan-4-one
• CAS: 1423038-38-3
• 化学式: C₂₉H₃₂O₆S
• 分子量: 508.635
• InChiKey: JKZPQJUEYRDRAE-NLDZOOGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,3R)-3-[(4-methoxyphenyl)methoxy]-2-[(4-methoxyphenyl)methoxymethyl]-2,3-dihydropyran-4-one 、 苄硫醇 在 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 1.5h， 以84%的产率得到
  参考文献：
  名称：

  Synthesis of α-2-deoxy-ulosides by Michael addition of hex-1-en-3-ones

  摘要：

  alpha-2-Deoxyulosides were synthesized in moderate to good yields by Michael addition of various O-nucleophiles to hex-1-en-3-ones in the presence of NaOH. These glycosyl additions were complete in 30 min at room temperature with high alpha-stereoselectivity in 53-92% yield. In addition, high alpha-stereoselectivity was also observed when S-nucleophiles were examined at 0 degrees C for 90 min. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.085

文献信息

• Synthesis of α-2-deoxy-ulosides by Michael addition of hex-1-en-3-ones
  作者：Zi-Ping Lin、Fung Fuh Wong、Yen-Bo Chen、Yu-Cheng Lin、Masayuki Kimura、Kimiyoshi Kaneko、Hiroyuki Takayama、Jin Bin Wu、Chun-Hung Lin、Hui-Chang Lin

  DOI：10.1016/j.tet.2012.12.085

  日期：2013.3

  alpha-2-Deoxyulosides were synthesized in moderate to good yields by Michael addition of various O-nucleophiles to hex-1-en-3-ones in the presence of NaOH. These glycosyl additions were complete in 30 min at room temperature with high alpha-stereoselectivity in 53-92% yield. In addition, high alpha-stereoselectivity was also observed when S-nucleophiles were examined at 0 degrees C for 90 min. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.