penta-N,O-acetyl-(+)-validamine | 68108-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: penta-N,O-acetyl-(+)-validamine
• 英文别名: pentaacetylvalidamine；[(1R,2R,3S,4S,5S)-5-acetamido-2,3,4-triacetyloxycyclohexyl]methyl acetate
• CAS: 68108-50-9
• 化学式: C₁₇H₂₅NO₉
• 分子量: 387.387
• InChiKey: KOOWXFYUPXIRQJ-ALYAQQCSSA-N

物化性质

• 沸点：
  492.8±34.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  penta-N,O-acetyl-(+)-validamine 以90%的产率得到
  参考文献：
  名称：

  YOSHIKAWA, MASAYUKI;CHA, BAE CHEON;OKAICHI, YOSHIHIKO;TAKINAMI, YOSHIHIKO+, CHEM. AND PHARM. BULL., 36,(1988) N 10, C. 4236-4239

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-bromo-6-deoxy-5a-carba-β-DL-glucopyranosyl bromide 在 sodium azide 、 硫化氢 、 氢溴酸 、 对甲苯磺酸 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 penta-N,O-acetyl-(+)-validamine
  参考文献：
  名称：

  （+）-（1,2,3 / 4,5）-2,3,4,5-四羟基环己烷-1-甲醇和（+）-（1,3 / 2,4,5）-5的全合成-氨基-2,3,4-三羟基环己烷-1-甲醇[（+）-有效胺]。（3 S）-（+）-2- exo -bromo-4,8-​​dioxatricyclo [4.2.1.O] nonan-5-one的X射线晶体结构

  摘要：

  （±）-7-内-氧杂双环[2.2.1]庚-5-烯-2-羧酸（±）-（1）的光学拆分已通过使用（R）-（+）-和（S）-（-）-α-甲基苄胺。（-）-（1）的绝对构型是根据对其衍生的溴内酯（2）的X射线分析确定的。标题支链环醇（6），由链霉菌属产生的抗生素。MA-4145已完全由（–）-（1）合成，其绝对构型已确定。所述五的合成Ñ，ö还通过（-）-（1）进行了（+）-有效胺的-乙酰基衍生物（12），该胺是通过抗生素有效霉素A降解获得的支链氨基环糖醇。

  DOI：

  10.1039/p19850000903

文献信息

• Stereoselective conversion of D-glucuronolactone into pseudo-sugar: Syntheses of pseudo -α-D-glucopyranose, pseudo-β-D-glucopyranose, and validamine
  作者：Masayuki Yoshikawa、Nobutoshi Murakami、Yoshihiro Yokokawa、Yasunao Inoue、Yasuyuki Kuroda、Isao Kitagawa

  DOI：10.1016/s0040-4020(01)85530-7

  日期：1994.1

  pseudo-β -D-glucopyranose (13), were synthesized from D-glucuronolactone in favorable overall yields by using a stereoselective nitromethane addition reaction and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps. Furthermore, a biologically active pseudo-aminosugar, validamine (18) was efficiently synthesized via a substitution reaction for an acetoxyl group at the β-position of nitro

  通过立体选择性硝基甲烷加成反应和还原消除反应，由D-葡糖醛酸内酯合成了两种旋光性假糖，即假α-D-吡喃葡萄糖（12）和假β-D-吡喃葡萄糖（13）。 NaBH 4作为关键步骤的乙氧基乙氧基部分的制备。此外，生物活性伪-aminosugar，validamine（18）中的有效地合成通过一个乙酰氧基在硝基的β位的nitrocyclitol衍生物（取代反应14，将其从合成中间体制备）（9）假-D-吡喃葡萄糖（12、13）。
• Syntheses of pseudo-.ALPHA.-D-glucopyranose, pseudo-.BETA.-D-glucopyranose, and validamine from D-glucuronolactone.
  作者：Masayuki YOSHIKAWA、Nobutoshi MURAKAMI、Yasunao INOUE、Yasuyuki KURODA、Isao KITAGAWA

  DOI：10.1248/cpb.41.1197

  日期：——

  Using a stereoselective nitromethane addition and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps, two optically active pseudo-sugars, pseudo-α-D-glucopyranose and pseudo-β-D-glucopyranose, were synthesized from D-glucuronolactone in favorable overall yield. Furthermore, a biologically active pseudo-aminosugar, validamine, was synthesized via a substitution reaction for an acetoxyl group at the β-position of the nitro group in the nitrocyclitol derivative which was prepared from a synthetic intermediate of pseudo-D-glucopyranose.

  通过立体选择性的硝基甲烷加成和用NaBH4还原消除乙氧基乙氧基官能团作为关键步骤，从D-葡萄糖醛酸内酯合成了两种光学活性的伪糖，伪-α-D-葡萄糖吡喃糖和伪-β-D-葡萄糖吡喃糖，获得了较好的总体产率。此外，通过对由伪-D-葡萄糖吡喃糖合成中间体制备的硝基环醇衍生物中硝基位置β位的乙酰氧基进行取代反应，合成了具有生物活性的伪氨基糖有效胺。
• Electrochemical Evaluation of Interaction between Avidin and Biotin Self-assembled Using Marker Ions
  作者：Hideki Kuramitz、Kazuharu Sugawara、Hiroshi Nakamura、Shunitz Tanaka

  DOI：10.1246/cl.1999.725

  日期：1999.8

  The interaction between avidin and biotin as self-assembled monolayer on a gold electrode surface was electrochemically evaluated by monitoring the changes in the electrode response of the ferrocyanide ion as redox-marker. It was clarified that the permeability changes of avidin membrane introduced onto the biotin self-assembled monolayer against ferrocyanide ion were ascribed to electrostatic interaction between avidin and marker ion.

  亲和素与生物素在金电极表面形成自组装单分子层的相互作用通过监测铁氰化物离子的电极响应变化进行了电化学评估。研究表明，引入到生物素自组装单分子层上的亲和素膜对铁氰化物离子的渗透性变化是由于亲和素与标记离子之间的静电相互作用所致。
• Synthetic Studies on the Validamycins. I. Synthesis of β-D-Glucopyranosylvalidamine: 1L-2-<i>O</i>-(β-D-Glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol
  作者：Seiichiro Ogawa、Yasuhito Shibata、Noritaka Chida、Tetsuo Suami

  DOI：10.1246/bcsj.56.494

  日期：1983.2

  β-D-Glucopyranosylvalidamine, the structure of which had first been assigned to a degradation product of validamycin A, was synthesized by condensation of a protected validamine with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, followed by removal of protecting groups. The synthesized β-D-glucopyranoside was not identical with an authentic sample derived from the antibiotic.

  β-D-吡喃葡萄糖基有效胺，其结构首先被指定为有效霉素 A 的降解产物，通过受保护的有效胺与 2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基缩合合成溴，然后去除保护基团。合成的 β-D-吡喃葡萄糖苷与源自抗生素的真实样品不同。
• SYNTHESIS OF β-D-GLUCOPYRANOSYLVALIDAMINE: 2-<i>O</i>-β-D-GLUCOPYRANOSYL-1L-(1,3,4/2,6)-4-AMINO-6-HYDROXYMETHYL-1,2,3-CYCLOHEXANETRIOL
  作者：Seiichiro Ogawa、Yasuhito Shibata、Noritaka Chida、Tetsuo Suami

  DOI：10.1246/cl.1980.135

  日期：1980.2.5

  β-D-Glucopyranosylvalidamine (1a), the structure of which was assigned to the degradation product of validamycin A, was synthesized by condensation of a protected validamine (8) with acetobromoglucose, followed by deblocking. Unexpectedly, 1a was found not to be identical with an authentic sample derived from the antibiotic.

  β-D-吡喃葡萄糖基有效胺 (1a)，其结构归属于有效霉素 A 的降解产物，通过受保护的有效胺 (8) 与乙酰溴葡萄糖缩合，然后解封来合成。出乎意料的是，发现 1a 与来自抗生素的真实样本不同。