2,3,4,5-di-O-isopropylidene-L-xylose diethyl dithioacetal | 192753-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,5-di-O-isopropylidene-L-xylose diethyl dithioacetal
• 英文别名: (4S,5R)-4-[bis(ethylsulfanyl)methyl]-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• CAS: 192753-59-6
• 化学式: C₁₅H₂₈O₄S₂
• 分子量: 336.517
• InChiKey: AQOSDHFQHXQKBE-TUAOUCFPSA-N

物化性质

• 沸点：
  404.3±40.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,5-di-O-isopropylidene-L-xylose diethyl dithioacetal 在 sodium hydride 、 mercury(II) oxide 、 magnesium chloride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 4.75h， 生成 1,2,3,4-bis-O-(1-methylethylidene)-5-O-(phenylmethyl)-5-C-2-thiazolyl-(5S)-D-xylitol
  参考文献：
  名称：

  [EN] SACCHARIDE CONJUGATES
  [FR] CONJUGUÉS SACCHARIDIQUES

  摘要：

  这项发明涉及包含糖苷共轭到成像剂或报告基团的化合物，包含它们的组合物以及使用它们的方法。具体提供了含有不同连接基团和成像剂或报告基团的BLM-二糖和BLM-单糖共轭物，用于靶向和成像肿瘤。

  公开号：

  WO2014152718A1
• 作为产物：
  描述：

  L-木糖 在 盐酸 作用下， 反应 5.25h， 生成 2,3,4,5-di-O-isopropylidene-L-xylose diethyl dithioacetal
  参考文献：
  名称：

  Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars:  l-Gulose, l-Idose, and the Disaccharide Subunit of Bleomycin A₂

  摘要：

  The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation-reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-alpha-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A(2).

  DOI：

  10.1021/jo970601h

文献信息

• [EN] SACCHARIDE CONJUGATES<br/>[FR] CONJUGUÉS SACCHARIDIQUES
  申请人：UNIV ARIZONA

  公开号：WO2014152718A1

  公开（公告）日：2014-09-25

  This invention relates to compounds comprising a saccharide conjugated to an imaging agent or a reporter group, compositions comprising them and methods of using them. Specifically BLM-disaccharide and BLM-monosaccharide conjugates containing different linker groups and an imaging agent or a reporter group are provided for the targeting and imaging of tumors.

  这项发明涉及包含糖苷共轭到成像剂或报告基团的化合物，包含它们的组合物以及使用它们的方法。具体提供了含有不同连接基团和成像剂或报告基团的BLM-二糖和BLM-单糖共轭物，用于靶向和成像肿瘤。
• Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars:  <scp>l</scp>-Gulose, <scp>l</scp>-Idose, and the Disaccharide Subunit of Bleomycin A₂
  作者：Alessandro Dondoni、Alberto Marra、Alessandro Massi

  DOI：10.1021/jo970601h

  日期：1997.9.1

  The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation-reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-alpha-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A(2).