3-deoxy-D-arabino-hexono-1,4-lactone | 50480-80-3

• 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: 3-deoxy-D-arabino-hexono-1,4-lactone
• 英文别名: D-arabino-3-deoxy-hexonic acid 4-lactone；D-arabino-3-Desoxy-hexonsaeure-4-lacton；3-deoxy-D-mannonolactone；(3S,5S)-5-[(1R)-1,2-dihydroxyethyl]-3-hydroxyoxolan-2-one
• CAS: 50480-80-3
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: NSEFGBGANVMEIR-LMVFSUKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  3-deoxy-D-arabino-hexono-1,4-lactone 在 camphor-10-sulfonic acid 2-甲基-2-丁烯 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 生成 3-deoxy-1,2:5,6-di-O-isopropylidene-β-D-arabino-hexofuranose
  参考文献：
  名称：

  Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

  摘要：

  Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-l,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-riho-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00018-5
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 palladium on activated charcoal sodium hydroxide 、 高氯酸 、 氢气 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 3.5h， 生成 3-deoxy-D-arabino-hexono-1,4-lactone
  参考文献：
  名称：

  Bock, Klaus; Lundt, Inge; Pedersen, Christian, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 3, p. 155 - 162

  摘要：

  DOI：

文献信息

• Production of aldoses
  申请人：Mitsui Chemicals, Inc.

  公开号：US20040254368A1

  公开（公告）日：2004-12-16

  An aldose having n-1 carbon atoms is produced from an aldonic acid having n carbon atoms using hypochlorous acid or a hypochlorite in a high yield at low cost with safety, by treating the reaction mixture with a compound having reactivity with the hypochlorous acid or hypochlorite higher than that with the produced aldose.

  使用次氯酸或次氯酸盐，通过将反应混合物与一种具有比产生的醛糖更高的次氯酸或次氯酸盐反应性的化合物处理，在低成本、安全且高产率下，可以从具有n个碳原子的醛酸产生具有n-1个碳原子的醛糖。
• Improved preparation and synthetic uses of 3-deoxy-d-arabino-hexonolactone: an efficient synthesis of Leptosphaerin
  作者：Christian Pedersen

  DOI：10.1016/s0008-6215(99)00007-5

  日期：1999.1

  Abstract Acetylation of d -glucono-1,5-lactone and subsequent treatment with triethylamine gave 2,4,6-tri-O-acetyl- d -erythro-hex-2-enono-1,5-lactone. Hydrogenation of the latter in the presence of palladium on carbon yielded 2,4,6-tri-O-acetyl-3-deoxy- d -arabino-hexono-1,5-lactone (5) in almost quantitative yield calculated from gluconolactone. Catalytic hydrogenation of 5 with platinum on carbon

  摘要d-葡萄糖基-1,5-内酯乙酰化并随后用三乙胺处理，得到2,4,6-三-O-乙酰基-d-赤型-己基-2-enono-1,5-内酯。在钯/碳存在下，后者的氢化反应产生了由葡糖酸内酯计算出的几乎定量的产率的2,4,6-三-O-乙酰基-3-脱氧-d-阿拉伯糖基己基-1,5-内酯（5）。在三乙胺的存在下，用铂在碳上催化氢化5，得到定量的2,4,6-三-O-乙酰基-3-脱氧-d-阿拉伯糖基己糖。5的脱乙酰基产生3-deoxy-d-阿拉伯-己基-1,4-内酯，将其转化为3-deoxy-5,6-6-O-异亚丙基-2-O-甲磺酰基-d-arabino-hexono-1， 4-内酯（10）。后者被转化为2-乙酰氨基-2,3-二脱氧-d-赤-己基-2-enono-1,4-内酯（Leptosphaerin）。当10在酸的存在下在水中煮沸时，
• A two step synthesis of 3-deoxy-d- or l-glycono-1,4-lactones and 2-0-alkyl-3-deoxy-d-glycono-1,4-lactones from d- or l-glyconolactones
  作者：Caroline Choquet-Farnier、Imane Stasik、Daniel Beaupère

  DOI：10.1016/s0008-6215(97)00164-x

  日期：1997.9

  Treatment of unprotected D-or L-glyconolactones with sodium hydride and alkyl halides, in dimethylsulfoxide, led to the corresponding 2-O-alkyl-3-deoxy-2-enono-1,4-lactones. Hydrogenolysis of 2-O-benzyl derivatives by catalytic hydrogen transfer with palladium on charcoal and cyclohexene as hydrogen donor gave 3-deoxy-hex- or pent-2-enono-1,4-lactones in the enolic forms. Reduction of 2-O-benzyl-enonolactones with ammonium formate as hydrogen donor afforded 3-deoxy-D- or L-glycono-1,4-lactones when 2-O-alkyl ethers gave the corresponding ethers. (C) 1997 Elsevier Science Ltd.
• The degradation of carbohydrates by alkali. Part III. 3-O-methyl derivatives of glucose and fructose
  作者：J. Kenner、G. N. Richards

  DOI：10.1039/jr9540000278

  日期：——
• 651. The reaction of phenyl- and 2,4-dinitrophenyl-hydrazine with some unsaturated glucose derivatives
  作者：W. M. Corbett

  DOI：10.1039/jr9590003213

  日期：——