1-benzyl-4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranoside-3-ulose | 178425-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzyl-4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranoside-3-ulose
• 英文别名: benzyl 4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranosid-3-ulose；[(2R,3R,6S)-3-acetyloxy-4-oxo-6-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 178425-80-4
• 化学式: C₁₇H₂₀O₇
• 分子量: 336.342
• InChiKey: MAKQRQXJAOJHGZ-IKGGRYGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1-benzyl-4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranoside-3-ulose 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (2R,3S,4S,6S)-6-Benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  α - O-和-S -2-脱氧糖苷的合成中的Michael型加成

  摘要：

  包括半乳糖，丝氨酸和半胱氨酸衍生物在内的O-和S-Nucleophiles经过对hexa-1-en-3-ulose进行MICHAEL型加成，以立体选择性地提供α-2-deoxy-ulosides。用NaBH 4可以选择性地降低C-3处的酮基功能。取决于CeCl 3的存在与否，可以获得两种配置。糖基化发生在DBU（1,8-二氮杂双环[5.4.0]十一碳-7-烯）催化的碱或KCN / 18-crown-6或ZnI 2催化的酸中。

  DOI：

  10.1016/0040-4039(96)00616-8
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 hydroxy(tosyloxy)iodobenzene 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 2.0h， 生成 1-benzyl-4,6-di-O-acetyl-2-deoxy-α-D-erythro-hexopyranoside-3-ulose
  参考文献：
  名称：

  α - O-和-S -2-脱氧糖苷的合成中的Michael型加成

  摘要：

  包括半乳糖，丝氨酸和半胱氨酸衍生物在内的O-和S-Nucleophiles经过对hexa-1-en-3-ulose进行MICHAEL型加成，以立体选择性地提供α-2-deoxy-ulosides。用NaBH 4可以选择性地降低C-3处的酮基功能。取决于CeCl 3的存在与否，可以获得两种配置。糖基化发生在DBU（1,8-二氮杂双环[5.4.0]十一碳-7-烯）催化的碱或KCN / 18-crown-6或ZnI 2催化的酸中。

  DOI：

  10.1016/0040-4039(96)00616-8

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.
• 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.