1-S-benzyl-2-deoxy-4,6-di-O-benzyl-α-D-erythro-hexopyranos-3-ulose | 1423038-31-6

• 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-benzyl-2-deoxy-4,6-di-O-benzyl-α-D-erythro-hexopyranos-3-ulose
• 英文别名: 1-S-benzyl 4,6-di-O-benzyl-2-deoxy-α-D-erythro-1-thio-hexopyranosid-3-ulose；(2R,3R,6R)-6-benzylsulfanyl-3-phenylmethoxy-2-(phenylmethoxymethyl)oxan-4-one
• CAS: 1423038-31-6
• 化学式: C₂₇H₂₈O₄S
• 分子量: 448.583
• InChiKey: DFAQYNBFOGMMPT-PFBJBMPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苄硫醇 、 (2R,3R)-3-(benzyloxy)-2-((benzyloxy)methyl)-2,3-dihydro-4H-pyran-4-one 在 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 1.5h， 以88%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

• New metal-free one-pot synthesis of α-2-deoxy-Ulosides by microwave-assisted double Michael Addition of β-enamino ketones
  作者：Pin-Chun Lin、Zi-Ping Lin、Po-Yen Chen、Min-Tsang Hsieh、Hui-Chang Lin

  DOI：10.1016/j.carres.2022.108712

  日期：2023.1

  New metal-free one-pot synthesis of α-2-deoxy-ulosides in moderate to good yields by microwave-assisted double Michael addition of various O-nucleophiles to β-enamino ketones in the presence of 12 N HCl. These glycosyl additions occurred with high α-stereoselectivity and were complete in 10–25 min in 51–93% yield. In addition, high α-stereoselectivity was also observed when S-nucleophiles were examined

  在 12  N HCl存在下，通过微波辅助将各种O-亲核试剂双迈克尔加成到 β-烯胺酮中，以中等到良好的收率实现 α-2-脱氧-uloside 的新型无金属一锅法合成。这些糖基添加具有高 α-立体选择性，并在 10-25 分钟内完成，产率为 51-93%。此外，当检查S-亲核试剂时，也观察到高 α-立体选择性。
• 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.