3,4-O-isopropylidene-2-O-trifluoromethanesulfonyl-L-arabinono-1,5-lactone | 522608-65-7

• 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-2-O-trifluoromethanesulfonyl-L-arabinono-1,5-lactone
• 英文别名: [(3aS,7R,7aS)-2,2-dimethyl-6-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl] trifluoromethanesulfonate
• CAS: 522608-65-7
• 化学式: C₉H₁₁F₃O₇S
• 分子量: 320.243
• InChiKey: CPSWVTCAPJMFEV-HCWXCVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4-O-isopropylidene-2-O-trifluoromethanesulfonyl-L-arabinono-1,5-lactone 在 二异丁基氢化铝 、 三氟乙酸 、 lithium iodide 作用下， 以 二氯甲烷 、 水 、 甲苯 、 丁酮 为溶剂， 反应 24.58h， 生成 2-脱氧-D-阿拉伯吡喃糖
  参考文献：
  名称：

  2-Deoxy-l-ribose from an l-arabinono-1,5-lactone

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00738-3
• 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， 生成 3,4-O-isopropylidene-2-O-trifluoromethanesulfonyl-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

• 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.
• Templated scaffolds of cis- and trans-tetrahydrofuran γ-amino acids: γ-azido-β-hydroxy-tetrahydrofuran-2-carboxylates from pentono-δ-lactones
  作者：Gangadharar J. Sanjayan、Alistair Stewart、Shuji Hachisu、Raquel Gonzalez、Mark P. Watterson、George W.J. Fleet

  DOI：10.1016/s0040-4039(03)01415-1

  日期：2003.7

  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.
• 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.