Methyl 2,3-anhydro-5-O-trityl-α-D-lyxofuranoside | 142890-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Methyl 2,3-anhydro-5-O-trityl-α-D-lyxofuranoside
• 英文别名: (1S,2S,4R,5S)-2-methoxy-4-(trityloxymethyl)-3,6-dioxabicyclo[3.1.0]hexane
• CAS: 142890-37-7
• 化学式: C₂₅H₂₄O₄
• 分子量: 388.463
• InChiKey: IPTGADYNRWJWSJ-SBFWRKJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2,3-anhydro-5-O-trityl-α-D-lyxofuranoside 在 三乙烯二胺 、 正丁基锂 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 7.75h， 生成 Methyl 2-O-benzoyl-3-deoxy-3-phenylthiomethyl-5-O-trityl-α-D-arabino-pentofuranoside
  参考文献：
  名称：

  Synthesis of derivatives of methyl 3-deoxy-3-C-formyl-α-d-arabino-pentofuranoside

  摘要：

  Methyl 2,3-anhydro-alpha-D-lyxofuranoside and some 5-substituted derivatives react with 2-lithio-1,3-dithiane and phenylthiomethyl-lithium at both positions of the epoxide ring. but mainly at C-3. The ratio of the adducts is affected by the nature of the 5-substituent. Appropriate desulphuration reactions of the dithioacetal and sulphide functions in the adducts gave derivatives of methyl 3-deoxy-3-C-formyl-alpha-D-arabino-pentofuranoside.

  DOI：

  10.1016/s0008-6215(00)90576-7
• 作为产物：
  描述：

  三苯基氯甲烷 、 methyl 2,3-anhydro-α-D-lyxofuranoside 在 吡啶 作用下， 反应 48.0h， 以90%的产率得到Methyl 2,3-anhydro-5-O-trityl-α-D-lyxofuranoside
  参考文献：
  名称：

  Synthesis of derivatives of methyl 3-deoxy-3-C-formyl-α-d-arabino-pentofuranoside

  摘要：

  Methyl 2,3-anhydro-alpha-D-lyxofuranoside and some 5-substituted derivatives react with 2-lithio-1,3-dithiane and phenylthiomethyl-lithium at both positions of the epoxide ring. but mainly at C-3. The ratio of the adducts is affected by the nature of the 5-substituent. Appropriate desulphuration reactions of the dithioacetal and sulphide functions in the adducts gave derivatives of methyl 3-deoxy-3-C-formyl-alpha-D-arabino-pentofuranoside.

  DOI：

  10.1016/s0008-6215(00)90576-7

文献信息

• Synthesis of anomerically pure vinyl sulfone-modified pent-2-enofuranosides and hex-2-enopyranosides: a group of highly reactive Michael acceptors for accessing carbohydrate based synthons
  作者：Aditya Kumar Sanki、Tanmaya Pathak

  DOI：10.1016/s0040-4020(03)01059-7

  日期：2003.9

  from the derivatives of d-xylose. For the synthesis of α- and β-anomers of vinyl sulfone-modified hex-2-enopyranosides, a d-glucose derivative was selected over a d-allose derivative as the starting material because the former almost exclusively produced the required methyl pyranosides whereas the latter produced a mixture. All sulfides were converted to vinyl sulfone-modified carbohydrates by the sequential

  乙烯基砜改性的戊-2-烯呋喃糖苷的苄基或三苯甲基保护的α-和β-端基异构体的合成已通过适当掩蔽的甲基α - lyxo呋喃糖基环氧化合物或甲基β-核糖呋喃糖基环氧化合物的开环而引发。或通过苄基保护的3- O-甲苯磺酰基木糖呋喃糖苷和3- O-甲磺酰基核糖呋喃糖苷中离去基团的亲核取代被p-硫代甲酚。在后一组原料的情况下，α-和β-甲基糖苷仅由d-木糖的衍生物以几乎相等的比例形成。对于乙烯基砜改性的hex-2-enopyranosides的α和β端基异构体的合成，选择d-葡萄糖衍生物而不是d-阿洛糖衍生物作为起始原料，因为前者几乎只能生产所需的甲基吡喃糖苷，而后者产生了混合物。通过顺序应用氧化，甲磺酰化和碱诱导的消除反应，将所有硫化物均转化为乙烯基砜改性的碳水化合物。
• First synthesis and antiprotozoal activities of divinyl sulfone-modified carbohydrates
  作者：Tarun Kumar Pal、Tuli Dey、Arindam Chakrabarty、Debanjana Dey、Sudip K. Ghosh、Tanmaya Pathak

  DOI：10.1016/j.bmcl.2010.04.056

  日期：2010.6

  Divinyl sulfone-modified carbohydrates have been synthesized for the first time by reacting easily available carbohydrate epoxides with thioethanol in a regiospecific fashion. One of the modified divinyl sulfones initiated significant cell death in Entamoeba species and the influence of the anomeric configurations on the biological activities of these sugar-derived divinyl sulfones has been highlighted. The most active compound in this series was found to be devoid of any toxicity. (C) 2010 Published by Elsevier Ltd.
• Synthesis of derivatives of methyl 3-deoxy-3-C-formyl-α-d-arabino-pentofuranoside
  作者：Sylvie Benefice-Malouet、Paul L. Coe、Richard T. Walker

  DOI：10.1016/s0008-6215(00)90576-7

  日期：1992.5

  Methyl 2,3-anhydro-alpha-D-lyxofuranoside and some 5-substituted derivatives react with 2-lithio-1,3-dithiane and phenylthiomethyl-lithium at both positions of the epoxide ring. but mainly at C-3. The ratio of the adducts is affected by the nature of the 5-substituent. Appropriate desulphuration reactions of the dithioacetal and sulphide functions in the adducts gave derivatives of methyl 3-deoxy-3-C-formyl-alpha-D-arabino-pentofuranoside.