2,3,4,5-tetra-O-acetyl-L-arabinose | 5139-19-5

• 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: 2,3,4,5-tetra-O-acetyl-L-arabinose
• 英文别名: (-)-aldehydo L-arabinose 2,3,4,5-tetraacetate；2,3,4,5-tetra-O-acetyl-aldehydo-L-arabinose；tetra-O-acetyl-L-arabinose；tetraacetyl-al-L-arabinose；tetraacetylal-L-arabinose；tetra-O-acetyl-aldehydo-L-arabinose；[(2S,3S,4R)-2,3,4-triacetyloxy-5-oxopentyl] acetate
• CAS: 5139-19-5
• 化学式: C₁₃H₁₈O₉
• 分子量: 318.281
• InChiKey: ZYPMNZKYVVSXOJ-RWMBFGLXSA-N

物化性质

• 熔点：
  97 °C(Solv: water (7732-18-5))
• 沸点：
  410.2±45.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-acetyl-L-arabinose 在 羟胺 作用下， 生成 tetra-O-acetyl-aldehydo-L-arabinose oxime
  参考文献：
  名称：

  The Acetylation of Galactose Oxime

  摘要：

  DOI：

  10.1021/ja01335a084
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-L-arabinose diethyl dithioacetal 在 bis(acetylacetonate)oxovanadium 、 双氧水 、 sodium iodide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以76%的产率得到2,3,4,5-tetra-O-acetyl-L-arabinose
  参考文献：
  名称：

  VO(acac)2/H2O2/NaI: a mild and efficient combination for the cleavage of dithioacetal derivatives of sugars

  摘要：

  A wide variety of dithioacetal derivatives of sugars can be cleaved easily into the corresponding open-chain aldehydo sugars using an efficient combination of VO(acac)(2)/H2O2/NaI at 0-5 degrees C. Some of the salient features of this protocol are mild reaction conditions, good yields, short reaction times, easy work-up procedures, and non-involvement of toxic chemicals. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.006

文献信息

• A simple stereoselective one-pot synthesis of<i>C</i>-nucleosides by 1,3-dipolar cycloaddition of chiral azomethine imines prepared<i>in situ</i>
  作者：Marko Žličar、Branko Stanovnik、Miha Tišler

  DOI：10.1002/jhet.5570300507

  日期：1993.10

  9-dimethyl-7,8-dihydro-9H-pyrazolo[4,3-d]tetrazolo[1,5-b]-pyridazine) obtained by the cycloaddition of 2-diazopropane to 6-chlorotetrazolo[1,5-b]pyridazine, is transformed with protected or unprotected carbohydrates 2, 5, 7,9, 11, 13 and 15 in the presence of methyl acrylate (3) into the corresponding C-nucleosides 4,6,8,10,12,14 and 16. In this one-pot synthesis two new chiral centers are formed stereoselectively

  通过环加成反应得到的NH，NH-二氢环加合物1（6-氯-9,9-二甲基-7,8-二氢-9 H-吡唑并[4,3- d ]四唑并[1,5- b ]-哒嗪） 2-重氮丙烷至6- chlorotetrazolo [1,5的b ]哒嗪，转化有保护或未被保护的碳水化合物2,5，7,9，11，13和15中的丙烯酸甲酯（存在3）插入到相应ç -核苷4,6,8,10,12,14和16。在这种一锅法合成中，取决于C的手性，立体选择性地形成了两个新的手性中心碳水化合物中的醛基旁边的碳原子。
• Medicinal Foodstuffs. XVI. Sugar Beet. (3). Absolute Stereostructures of Betavulgarosides II and IV, Hypoglycemic Saponins Having a Unique Substituent, from the Roots of Beta vulgaris L.
  作者：Toshiyuki MURAKAMI、Hisashi MATSUDA、Masahiro INADZUKI、Kazuhiro HIRANO、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.47.1717

  日期：——

  The absolute stereostructures of betavulgaroside II having a dioxolane-type substituent and betavulgaroside IV having an acetal-type substituent, which were isolated from the roots of Beta vulgaris L. (sugar beet, Chenopodiaceae) and exhibited hypoglycemic activity on glucose-loaded rats, were determined by the chemical correlations of betavulgarosides II and IV with a known saponin, momordin I. In these chemical correlations, the α-L-arabinopyranosyl moiety of momordin I was converted to a dioxolane-type substituent of betavulgaroside II or to an acetal-type substituent of betavulgaroside IV. Additionally, the 2'-diastereoisomer of betavulgaroside IV was synthesized from momordin I, and four acetal-type substituent analogues were also synthesized from L- and D-arabinose.

  通过将已知皂苷 momordin I 与 betavulgaroside II 和 IV 进行化学关联，确定了从甜菜（藜科）根部分离出的具有对葡萄糖负荷大鼠的降血糖活性的含有二氧六环型取代基的 betavulgaroside II 和含有缩酮型取代基的 betavulgaroside IV 的绝对立体结构。在这些化学关联中，momordin I 的 α-L-阿拉伯糖苷部分被转化为 betavulgaroside II 的二氧六环型取代基或 betavulgaroside IV 的缩酮型取代基。此外，从 momordin I 合成了 betavulgaroside IV 的 2'-非对映异构体，并从 L- 和 D-阿拉伯糖合成了四种缩酮型取代基类似物。
• New route to higher sugars
  作者：N.K. Kochetkov、B.A. Dmitriev

  DOI：10.1016/0040-4020(65)80013-8

  日期：1965.1

  A novel general route to higher aldoses is proposed involving transformation of the starting monosaccharides-2,3-dehydro-2-3-dideoxyaldonic acid or to its ester, by Knoevenage-Doebner condensation or Wittig reaction, folowed by double bond hydroxylation to give higher aldonic acids. The acids are reduced to the corresponding aldoses by conventional methods.

  提出了一种新的制备更高醛糖的一般方法，该方法涉及通过Knoevenage-Doebner缩合或Wittig反应将起始的单糖-2,3-脱氢-2-3-二脱氧醛糖醛酸或其酯转化，然后通过双键羟基化反应得到更高的醛糖。醛糖酸。通过常规方法将酸还原成相应的醛糖。
• Stereochemical aspects of the formation of diastereoisomeric 3-acetyl-2-(polyacetoxyalkyl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazoles
  作者：László Somogyi

  DOI：10.1016/0008-6215(88)84088-6

  日期：1988.10

  arabino -(tetra-acetoxybutyl)]- [(−)- and (+)- 4a , (−)- 4b ] and 3-acetyl-2-[ d - manno -(penta-acetoxypentyl)]-5-phenyl-2,3-dihydro-1,3,4-oxadiazoles [(+)- 4d ] via cyclisation of the corresponding ( O -acetylated) aldose benzoylhydrazones ( 2a,b,d ) under acetylating conditions is described. The stereochemical aspects of the formation of C-2 epimeric oxadiazolines [ e.g. , (−)- and (+)- 4a ] are discussed

  摘要d-和l -3-乙酰基-2- [阿拉伯-（四乙酰氧基丁基）]-[（-）-和（+）-4a，（-）-4b]和3-乙酰基-2-的合成[d-manno-（penta-acetoxypentyl）]-5-phenyl-2,3-dihydro-1,3,4-oxadiazoles [（+）-4d]通过相应的（O-乙酰化）醛糖苯甲酰hydr（2a描述了在乙酰化条件下的（b，d）。基于旋光度和核磁共振数据，讨论了C-2差向异构恶二唑啉[例如，（-）-和（+）-4a]形成的立体化学方面。发现甲基乙二醛双（苯甲酰基hydr）（8）的乙酰化得到非对映异构的1,3,4-恶二唑啉（12a和12b），而不是文献中要求的双（乙酰​​苯甲酰hydr）9。
• Aldose-aminoguanidine condensation products: syntheses and n.m.r. studies
  作者：Lászlo Szilágyi、Zoltán Györgydeák、Helmut Duddeck

  DOI：10.1016/0008-6215(86)84006-x

  日期：1986.12

  Abstract The condensation products of aldoses with aminoguanidine exist in aqueous solution at pH 6 as cyclic pyranosylaminoguanidines with the protonated aminoguanidine substituent at C-1 equatorial, and at pH 12 and in methyl sulfoxide as acyclic E -carboximidamidehydrazones. The cyclic isomers are present exclusively when mineral acid salts of the condensation products are dissolved in methyl sulfoxide

  摘要醛糖与氨基胍的缩合产物在pH 6的水溶液中以环状吡喃糖基氨基胍存在，在C-1赤道处为质子化的氨基胍取代基，在pH 12时以甲基亚砜的形式存在于无环的E-羧酰亚胺酰胺hydr中。当缩合产物的无机酸盐溶于甲基亚砜时，仅存在环状异构体。已通过1 H-，13 C-和15 Nn.mr方法研究了氨基胍部分的质子化和互变异构位点，并讨论了pH依赖性环-非环互变的机理。