3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone | 116730-60-0

• 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: 3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone
• 英文别名: (3aR,4R,7S,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 116730-60-0；137126-24-0；137126-25-1；137126-26-2；137126-27-3；137126-31-9；137126-32-0；116730-59-7
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: HQVJTKTXELKPID-ZOZBQHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone 在 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 以 丙酮 为溶剂， 反应 32.0h， 生成 2,3:6,7-Di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone
  参考文献：
  名称：

  Acetonides of heptonolactones: Powerful chirons

  摘要：

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.

  DOI：

  10.1016/s0957-4166(00)82201-6
• 作为产物：
  描述：

  D-mannose 在 硫酸 作用下， 以 水 为溶剂， 反应 9.0h， 生成 3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone
  参考文献：
  名称：

  Acetonides of heptonolactones: Powerful chirons

  摘要：

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.

  DOI：

  10.1016/s0957-4166(00)82201-6

文献信息

• Cyclic sulphates of δ-lactones in the synthesis of tetrahydrofurans tetrahydropyrans and cyclohexanes
  作者：Ben M. Skead、George W.J. Fleet、John Saunders、R. Brian Lamont

  DOI：10.1016/s0040-4039(00)61744-6

  日期：1993.9

  Side-chain cyclic sulphates derived from a δ-lactone (1) provide easy access to complex tetrahydrofuran, tetrahydropyran and cyclohexane derivatives each with 5 adjacent chiral centres and at least 6 adjacent carbons bearing functional groups.

  衍生自δ-内酯（1）的侧链环状硫酸盐可轻松获得复杂的四氢呋喃，四氢吡喃和环己烷衍生物，每个衍生物均具有5个相邻的手性中心和至少6个相邻的带有官能团的碳。
• Structural essentials for β-N-acetylhexosaminidase inhibition by amides of prolines, pipecolic and azetidine carboxylic acids
  作者：A. F. G. Glawar、R. F. Martínez、B. J. Ayers、M. A. Hollas、N. Ngo、S. Nakagawa、A. Kato、T. D. Butters、G. W. J. Fleet、S. F. Jenkinson

  DOI：10.1039/c6ob01549b

  日期：——

  design and synthesis of β-N-acetylhexosaminidase inhibitors along with their applicability to human disease treatment through biological evaluation in both an enzymatic and cellular setting. We investigated the importance of individual stereocenters, variations in structure–activity relationships along with factors influencing cell penetration. To achieve these goals we modified nitrogen heterocycles

  本文探讨了计算机建模辅助设计和合成β- N-乙酰基己糖胺酶抑制剂的方法，以及它们在酶和细胞环境中通过生物学评估在人类疾病治疗中的适用性。我们研究了各个立体中心的重要性，结构-活性关系的变化以及影响细胞渗透的因素。为了实现这些目标，我们根据环的大小，存在的侧链和环氮的衍生化改性了氮杂环。通过将抑制剂与活性位点的相互作用降低到最低限度，我们能够确定除已建立的2 S，3 R反式关系外，CH 2的存在和立体化学OH侧链对于活性至关重要。就细胞渗透而言，N-丁基侧链有利于细胞吸收，而环氮上带有羟基和羧基的侧链则阻碍细胞渗透。此外，我们显示了原理研究的早期证据，即β- N-乙酰基己糖胺酶抑制剂可适用于潜在的抗侵袭性抗癌策略。
• Iminoheptitols as glycosidase inhibitors: Synthesis of, and mannosidase and fucosidase inhibition by, α—homomannojirimycin and 6-epi-homomannojirimycin
  作者：Ian Bruce、George W.J. Fleet、Isabelle Cenci di Bello、Bryan Winchester

  DOI：10.1016/s0040-4039(01)93952-8

  日期：1989.1

  C-2 and C-6 of a heptonolactone are joined together by nitrogen to afford α-homomannojirimycin (HMJ) and 6-epi-α-homomannojirimycin; the inhibition of some α-mannosidases and α-fucosidases by these iminoheptitols is reported.

  庚内酯的C-2和C-6通过氮连接在一起，得到α-同甘露糖霉素（HMJ）和6-e-α-同甘露糖霉素；据报道，这些亚氨基庚糖醇对某些α-甘露糖苷酶和α-岩藻糖苷酶具有抑制作用。
• A practical synthesis of 2-deoxy aldonolactones via a SmI2-mediated α-deoxygenation reaction
  作者：Stephen Hanessian、Christian Girard、Jose Luis Chiara

  DOI：10.1016/s0040-4039(00)92313-x

  日期：1992.1

  A one-step deoxygenation of 2-hydroxylactones or their acetates is possible using samarium diiodide as an electron-transfer reagent in conjunction with a proton source.
• Eight Stereoisomers of Homonojirimycin from <scp>d</scp>-Mannose
  作者：Gabriel M. J. Lenagh-Snow、Sarah F. Jenkinson、Scott J. Newberry、Atsushi Kato、Shinpei Nakagawa、Isao Adachi、Mark R. Wormald、Akihide Yoshihara、Kenji Morimoto、Kazuya Akimitsu、Ken Izumori、George W. J. Fleet

  DOI：10.1021/ol3005744

  日期：2012.4.20

  Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from D-mannose allow the synthesis in water of eight stereoisomers of HNJ.