3,4-O-isopropylidene-L-arabinono-1,5-lactone | 40031-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4-O-isopropylidene-L-arabinono-1,5-lactone
• 英文别名: L-Arabinonic acid, 3,4-O-(1-methylethylidene)-, delta-lactone；(3aS,7R,7aR)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 40031-40-1
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: UNYKZJZFOKUHEK-JKUQZMGJSA-N

物化性质

• 熔点：
  92 °C(Solv: ligroine (8032-32-4))
• 沸点：
  356.7±42.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-O-isopropylidene-L-arabinono-1,5-lactone 在 palladium on activated charcoal 氢氧化钾 、 高氯酸 、 甲基锂 、 氢气 、 silver(l) oxide 作用下， 以 乙醚 、 乙醇 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 5.33h， 生成 1,2:4,5-di-O-isopropylidene-β-L-fructopyranose
  参考文献：
  名称：

  Iodomethyl Group as a Hydroxymethyl Synthetic Equivalent:  Application to the Syntheses of d-manno-Hept-2-ulose and l-Fructose Derivatives

  摘要：

  The one-carbon elongation of aldoses to ketoses using iodomethyllithium as the key reagent in the homologation step is exemplified by the preparation of two carbohydrates of chemical and biological interests: (D)-manno-hept-2-ulose from (D)-mannose and (L)-fructose from (L)-arabinose.

  DOI：

  10.1021/jo0342166
• 作为产物：
  描述：

  3,4-O-isopropylidine L-arabinopyranose 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以58%的产率得到3,4-O-isopropylidene-L-arabinono-1,5-lactone
  参考文献：
  名称：

  Templated scaffolds of cis- and trans-tetrahydrofuran γ-amino acids: γ-azido-β-hydroxy-tetrahydrofuran-2-carboxylates from pentono-δ-lactones

  摘要：

  Short syntheses of enantiomeric templated scaffolds of cis- and trans-tetrahydrofuran gamma-amino acids from pentono-delta-lactones derived from arabinose and ribose are reported; an unexpectedly efficient synthesis of a templated tetrahydrofuran beta-amino acid by azide displacement of a triflate beta to an ester function proceeds with remarkably little elimination. These materials should allow evaluation of such peptidomimetics to induce predisposition towards secondary structures. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01415-1

文献信息

• Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones
  作者：So-Yeop Han、Madeleine M. Joullié、Valery V. Fokin、Nicos A. Petasis

  DOI：10.1016/s0957-4166(00)80400-0

  日期：1994.12

  D-xylonolactone, D-lyxonolactone 2-deoxy-D-ribonolactone toward benzaldehyde and acetone in acidic media, were examined. The reactions involved complex equilibria and were investigated with extensive 13C NMR studies as well as X-ray crystallographic analysis of selected products. Molecular mechanics (MM2) and semiempirical (PM3 and AM1) calculations of some derivatives were carried out in order to facilitate structural

  检查了D-核糖内酯，L-阿拉伯糖内酯，D-木糖内酯，D-苯二酸内酯2-脱氧-D-核糖内酯在酸性介质中对苯甲醛和丙酮的不同反应性。反应涉及复杂的平衡，并通过广泛的13 C NMR研究以及所选产品的X射线晶体学分析进行了研究。为了方便结构和构象的分配，对某些衍生物进行了分子力学（MM2）和半经验（PM3和AM1）计算。D-戊烯-1,4-内酯与苯甲醛和丙酮反应的反应活性差异在结构和构象方面均得到合理化。
• High yield protection of alcohols, including tertiary and base sensitive alcohols, as benzhydryl ethers by heating with diphenyldiazomethane in the absence of any other reagent
  作者：Daniel Best、Sarah F. Jenkinson、Sebastian D. Rule、Rosemary Higham、Thomas B. Mercer、Richard J. Newell、Alexander C. Weymouth-Wilson、George W.J. Fleet、Sigthor Petursson

  DOI：10.1016/j.tetlet.2008.02.042

  日期：2008.3

  can be introduced efficiently without the need for any acid or base catalysis and which is not prone to acid or base catalysed migration is a significant advantage for many syntheses. Benzhydryl [diphenylmethyl] ethers of sugar lactones are formed in high yield under neutral conditions when the corresponding alcohol is heated with diphenyldiazomethane in an inert solvent such as acetonitrile or toluene;

  对于许多合成而言，可在不需要任何酸或碱催化的情况下有效地引入保护基且不易于被酸或碱催化的迁移的保护基是重要的优点。当相应的醇与二苯基重氮甲烷在惰性溶剂（如乙腈或甲苯）中加热时，在中性条件下，糖内酯的苄基[二苯基甲基]醚可以高收率形成；这样就可以在没有任何其他试剂的情况下轻松保护对碱敏感的和高度受阻的叔醇。
• Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of β-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols
  作者：Elizabeth V. Crabtree、R. Fernando Martínez、Shinpei Nakagawa、Isao Adachi、Terry D. Butters、Atsushi Kato、George W. J. Fleet、Andreas F. G. Glawar

  DOI：10.1039/c4ob00097h

  日期：——

  The enantiomers of XYLNAc (2-N-acetylamino-1,2,4-trideoxy-1,4-iminoxylitol) are prepared from the enantiomers of glucuronolactone; the synthesis of the enantiomers of LYXNAc (2-N-acetylamino-1,2,4-trideoxy-1,4-iminolyxitol) from an L-arabinono-δ-lactone and a D-ribono-δ-lactone is reported. A comparison is made of the inhibition of β-N-acetylhexosaminidases (HexNAcases) and α-N-acetylgalactosaminidase (α-GalNAcase) by 8 stereoisomeric 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols; their N-benzyl derivatives are better inhibitors than the parent compounds. Both XYLNAc and LABNAc are potent inhibitors against HexNAcases. None of the compounds show any inhibition of α-GalNAcase.

  XYLNAc（2-N-乙酰氨基-1,2,4-三脱氧-1,4-亚氨基木糖醇）的对映异构体由葡糖醛酸内酯的对映异构体制备；LYXNAc（2-N-乙酰氨基-1,2,4-三脱氧-1,4-亚氨基木糖醇）的对映异构体由L-阿拉伯糖酸-Γ-内酯和D-核糖酸-Γ-内酯合成。对8种立体异构体2-N-乙酰氨基-1,2,4-三脱氧-1,4-亚氨基戊糖醇对β-N-乙酰氨基己糖苷酶（HexNAcase）和α-N-乙酰氨基半乳糖苷酶（α-GalNAcase）的抑制作用进行了比较；它们的N-苄基衍生物比母体化合物是更好的抑制剂。XYLNAc和LABNAc都是HexNAcase的强效抑制剂。这些化合物对α-GalNAcase均无抑制作用。
• Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships
  作者：Alison A. Edwards、Gangadharar J. Sanjayan、Shuji Hachisu、Raquel Soengas、Alistair Stewart、George E. Tranter、George W.J. Fleet

  DOI：10.1016/j.tet.2006.02.007

  日期：2006.4

  Templated tetrahydrofuran-based gamma-azido esters were prepared with the C-2 and C-4 functionalities in cis and trans relative configurations. This was achieved by ring contraction of the suitably protected 2-O-triflates of pentono-1,5-lactones (D-ribose and L-arabinose) with subsequent introduction of the azide via the 4-O-triflate. Access to a corresponding beta-azido ester was achieved in good yield. Little elimination product was observed by introduction of the azide via the 3-O-triflate. These azido esters are scaffolds. which may be predisposed to adopt secondary structural motifs, for example. for use as peptidomimetics; they may also be utilised for the preparation of stereodiverse compound libraries. (c) 2006 Elsevier Ltd All rights reserved.
• 2-Deoxy-l-ribose from an l-arabinono-1,5-lactone
  作者：Alistair J. Stewart、Richard M. Evans、Alexander C. Weymouth-Wilson、Andrew R. Cowley、David J. Watkin、George W.J. Fleet

  DOI：10.1016/s0957-4166(02)00738-3

  日期：2002.12

  A practical synthesis of 2-deoxy-L-ribose from L-arabinose depends on the efficient reduction by iodide of a triflate a to a lactone. The X-ray crystal structure of 3,4-O-isopropylidene-L-arabinono-1,5-tactone is reported. (C) 2002 Published by Elsevier Science Ltd.