(1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol | 14187-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol
• 英文别名: N,N'-diacetyl-2-deoxystreptamine；N,N'-Diacetyl-2-desoxy-streptamin, ；N,N'-Diacetyl-2-desoxy-streptamin ；Di-N-acetyl-2-desoxystreptamin
• CAS: 14187-81-6
• 化学式: C₁₀H₁₈N₂O₅
• 分子量: 246.263
• InChiKey: VSPGPQVWBDCERN-JEDPFWTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.52
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  118.89
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol 、 乙酸酐 在 吡啶 作用下， 生成 2-deoxystreptamine pentaacetate
  参考文献：
  名称：

  Yoshikawa, Masayuki; Ikeda, Yoshiharu; Kayakiri, Hiroshi, Heterocycles, 1982, vol. 17, p. 209 - 214

  摘要：

  DOI：
• 作为产物：
  描述：

  (1α,2β,3α,5α,7α)-2-Brom-4,8-dioxatricyclo<5.1.0.0^3,5>octan 在 palladium on activated charcoal 氨 、 氢气 、 一水合肼 、 硫酸肼 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 65.0h， 生成 (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol
  参考文献：
  名称：

  Kuehlmeyer, Rainer; Keller, Reinhold; Schwesinger, Reinhard, Chemische Berichte, 1984, vol. 117, # 5, p. 1765 - 1800

  摘要：

  DOI：

文献信息

• A chiral approach to 2-deoxystreptamine
  作者：Hans H. Baer、Isamu Arai、Bruno Radatus、June Rodwell、Nguyen Chinh

  DOI：10.1139/v87-246

  日期：1987.7.1

  A new synthesis of 2-deoxystreptamine (21), a component of numerous antibiotics, was developed. Starting from D-mannose, it proceeds through chiral intermediates and is designed to furnish starting points for the preparation of stereospecifically modified derivatives of the meso compound 21. 1,2-Dideoxy-1-nitro-D-manno-heptitol (2), obtainable from mannose by the nitromethane method, was protected as the 4,5:6,7-di-O-isopropylidene derivative 4, which was mesylated or triflated in position 3. From the sulfonic esters (5 and 6) two different routes involving displacement by azide, partial deacetonation at O-6,7, periodate oxidation, and cyclization of the resulting nitroaldohexose derivatives converged to give 1L-(1,3/2,4,6)-6-azido-1,2-O-isopropylidene-4-nitro-1,2,3-cyclohexanetriol (19) as a key intermediate. Catalytic hydrogenation then afforded optically active 4,5-O-isopropylidene-2-deoxystreptamine (23), isolated as its N,N′-diacetyl derivative 24. Deacetonation of 19 gave the azidonitrotriol 15, which was reduced to 21. The potential utility of the chiral intermediates for stereospecific syntheses of deoxystreptamine-containing aminoglycosides is discussed.

  开发了2-去氧链霉素（21）的新合成方法，该化合物是许多抗生素的组成部分。该方法从D-甘露糖开始，经过手性中间体，并设计为提供用于制备手性修饰的meso化合物21衍生物的起始点。可通过硝甲烷法从甘露糖获得1,2-二去氧-1-硝基-D-曼诺庚醇（2），然后保护为4,5:6,7-二-O-异丙基亚甲基（4），然后在3位进行甲烷基磺酸化或三氟甲磺酸化。从磺酸酯（5和6）出发，通过氮化物的置换、O-6,7的部分脱乙酰化、高碘酸氧化和环化反应，得到了1L-(1,3/2,4,6)-6-azido-1,2-O-异丙基亚甲基-4-硝基-1,2,3-环己三醇（19）作为关键中间体。催化氢化然后得到了光学活性的4,5-O-异丙基亚甲基-2-去氧链霉素（23），并以其N,N'-二乙酰衍生物24的形式分离。19的脱乙酰化得到了偶氮硝基三醇15，然后还原成21。讨论了手性中间体在合成含有2-去氧链霉素的氨基糖苷类化合物中的可能用途。
• Efficient Preparation of a 1,3-Diazidocyclitol as a Versatile 2-Deoxystreptamine Precursor
  作者：Guuske F. Busscher、Stan Groothuys、René de Gelder、Floris P. J. T. Rutjes、Floris L. van Delft

  DOI：10.1021/jo049788k

  日期：2004.6.1

  A synthesis route toward 2-deoxystreptamine, a common structure in many of the clinically important aminoglycosides, is presented. Starting from p-benzoquinone and cyclopentadiene, 2-deoxystreptamine is synthesized with key steps involving Pd(0)-catalyzed rearrangement, a retro-Diels-Alder by flash vacuum thermolysis, and Yb(III)-directed regioselective epoxide opening. The obtained diazidocyclitol 17 is a suitable 2-deoxystreptamine precursor, conveniently protected for incorporation in new aminoglycoside entities.
• Nitrogen-15 nuclear magnetic resonance spectroscopy of neomycin B and related aminoglycosides
  作者：Robert E. Botto、Bruce Coxon

  DOI：10.1021/ja00342a062

  日期：1983.2
• Dijkstra,D., Recueil des Travaux Chimiques des Pays-Bas, 1968, vol. 87, p. 161 - 180
  作者：Dijkstra,D.

  DOI：——

  日期：——