2-C-hydroxymethyl-D-mannono-1,4-lactone | 211623-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-C-hydroxymethyl-D-mannono-1,4-lactone
• 英文别名: (3S,4S,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-3-(hydroxymethyl)oxolan-2-one
• CAS: 211623-21-1
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: ZDNFJRRJLNVFHS-CXXDYQFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-C-hydroxymethyl-D-mannono-1,4-lactone 在 samarium diiodide 、 Dowex-50 (H(+) form) 作用下， 生成 (3S,4R,5S)-5-((R)-1,2-Dihydroxy-ethyl)-4-hydroxy-3-hydroxymethyl-dihydro-furan-2-one
  参考文献：
  名称：

  不涉及有机金属试剂的受保护的2-脱氧-2-羟甲基-d-甘露糖和-d-葡萄糖衍生物的制备

  摘要：

  摘要支链保护的糖2-C-羟甲基-2,3; 5,6-二-O-异亚丙基-d-甘露呋喃糖通过亚苯乙烯方法（93％）在伯羟基位置被专门苄基化。用氯铬酸吡啶鎓氧化，得到71％的产率的2-C-苄氧基甲基-2,3; 5,6-二-O-异亚丙基-d-甘露糖内酯，将其在环氧丙烷中用3当量的二碘化mar还原为56:44的混合物。该2-脱氧衍生物，2-C-苄氧基甲基-2-脱氧-5，6-O-异亚丙基-d-甘露糖基-（5）和-d-葡糖基内酯的总收率为83％。在二氯甲烷中用DIBAH还原内酯5得到保护的支链糖2-C-苄氧基-2-脱氧-5,6-O-异亚丙基-d-甘露糖，收率为63％。在2-C-羟甲基-2,3; 5的还原中，

  DOI：

  10.1016/s0008-6215(98)00080-9
• 作为产物：
  描述：

  2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone 在 三氟乙酸 作用下， 以 水 为溶剂， 以82%的产率得到2-C-hydroxymethyl-D-mannono-1,4-lactone
  参考文献：
  名称：

  Synthesis of 2-C-branched derivatives of d-mannose: 2-C-aminomethyl-d-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of d-mannose

  摘要：

  2-C-Substituted branched D-mannose analogues are novel monosaccharides, readily obtained from a Kiliani-acetonation sequence on D-fructose, followed by subsequent functional group manipulation. 2-C-Azidomethyl-D-mannose and 2-C-aminomethylD-marmose bind to the C-type lectin DC-SIGN (CD209) with significantly greater affinity than mannose. In particular, 2-C-aminomethyl-D-mannose exhibits a comparative 48-fold increase in binding as determined using a surface plasmon resonance-based competition assay. DC-SIGN is an important cell-surface type II transmembrane protein that interacts with blood group antigens, endogenous glycoproteins such as ICAM-3, and also deadly pathogens such as the human immunodeficiency and hepatitis C viruses. The effective use of small compounds to block target binding by mannose-selective C-type lectins at sub-millimolar concentrations has not been shown previously; thus, these data represent a very attractive thoroughfare to novel antiviral and immunomodulatory drug development. @ 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.003

文献信息

• Kiliani on ketoses: branched carbohydrate building blocks from d-fructose and l-sorbose
  作者：David Hotchkiss、Raquel Soengas、Michela Iezzi Simone、Jeroen van Ameijde、Stuart Hunter、Andrew R. Cowley、George W.J. Fleet

  DOI：10.1016/j.tetlet.2004.10.086

  日期：2004.12

  both cases, the readily crystallized diacetonides have a 2,3-cis-diol relationship in the product lactone. An efficient double inversion of the configuration at C-4 and C-5 of the product from d-fructose gives access to the formal Kiliani product from l-psicose. Branched carbohydrate lactones are likely to be of significant value as chirons for homochiral targets with functionalized quaternary centres

  经保护的支链糖内酯可通过Kiliani-丙酮化序列在容易获得的酮糖如d-果糖和l-山梨糖上获得。在两种情况下，容易结晶的二丙酮化物在产物内酯中具有2，3-顺-二醇关系。来自d-果糖的产物在C-4和C-5处的构型的有效两次转化使得能够获得来自l--糖的形式Kiliani产物。支链碳水化合物内酯作为具有功能化四元中心的同手性目标的卡隆，可能具有重要的价值。
• Synthesis of 2-C-branched derivatives of d-mannose: 2-C-aminomethyl-d-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of d-mannose
  作者：Daniel A. Mitchell、Nigel A. Jones、Stuart J. Hunter、Joseph M.D. Cook、Sarah F. Jenkinson、Mark R. Wormald、Raymond A. Dwek、George W.J. Fleet

  DOI：10.1016/j.tetasy.2007.06.003

  日期：2007.7

  2-C-Substituted branched D-mannose analogues are novel monosaccharides, readily obtained from a Kiliani-acetonation sequence on D-fructose, followed by subsequent functional group manipulation. 2-C-Azidomethyl-D-mannose and 2-C-aminomethylD-marmose bind to the C-type lectin DC-SIGN (CD209) with significantly greater affinity than mannose. In particular, 2-C-aminomethyl-D-mannose exhibits a comparative 48-fold increase in binding as determined using a surface plasmon resonance-based competition assay. DC-SIGN is an important cell-surface type II transmembrane protein that interacts with blood group antigens, endogenous glycoproteins such as ICAM-3, and also deadly pathogens such as the human immunodeficiency and hepatitis C viruses. The effective use of small compounds to block target binding by mannose-selective C-type lectins at sub-millimolar concentrations has not been shown previously; thus, these data represent a very attractive thoroughfare to novel antiviral and immunomodulatory drug development. @ 2007 Elsevier Ltd. All rights reserved.
• A preparation of protected 2-deoxy-2-hydroxymethyl-d-mannose and -d-glucose derivatives not involving organometallic reagents
  作者：Annie Malleron、Serge David

  DOI：10.1016/s0008-6215(98)00080-9

  日期：1998.3

  oxolane to a 56:44 mixture of the 2-deoxy derivatives, 2- C -benzyloxymethyl-2-deoxy-5,6- O -isopropylidene- d -mannono- ( 5 ) and - d -glucono-lactones in 83% combined yield. Reduction of lactone 5 with DIBAH in dichloromethane gave the protected branched chain sugar, 2- C -benzyloxy-2-deoxy-5,6- O -isopropylidene- d -mannose in 63% yield. In the reduction of 2- C -hydroxymethyl-2,3;5,6-di- O- isopropylidene-

  摘要支链保护的糖2-C-羟甲基-2,3; 5,6-二-O-异亚丙基-d-甘露呋喃糖通过亚苯乙烯方法（93％）在伯羟基位置被专门苄基化。用氯铬酸吡啶鎓氧化，得到71％的产率的2-C-苄氧基甲基-2,3; 5,6-二-O-异亚丙基-d-甘露糖内酯，将其在环氧丙烷中用3当量的二碘化mar还原为56:44的混合物。该2-脱氧衍生物，2-C-苄氧基甲基-2-脱氧-5，6-O-异亚丙基-d-甘露糖基-（5）和-d-葡糖基内酯的总收率为83％。在二氯甲烷中用DIBAH还原内酯5得到保护的支链糖2-C-苄氧基-2-脱氧-5,6-O-异亚丙基-d-甘露糖，收率为63％。在2-C-羟甲基-2,3; 5的还原中，