Propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 32748-46-2

• 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: Propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 3-carboxypropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butyric acid；4-(((2R,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butanoic acid；4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxybutanoic acid
• CAS: 32748-46-2
• 化学式: C₁₈H₂₆O₁₂
• 分子量: 434.397
• InChiKey: YWFYYAPQJAVDIL-SOVHRIKKSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  534.9±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙醇-2-氯碳酸酯(2:1) 、 Propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以96%的产率得到[3-[4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxybutanoyloxy]-2,2-bis[4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxybutanoyloxymethyl]propyl] 4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxybutanoate
  参考文献：
  名称：

  Synthesis of a symmetric multivalent molecule containing four carbohydrate substituents

  摘要：

  Starting with allyl- and pent-4-enyl-beta-D-glucopyranosides 4-7, different D-Glucose units (8-15) containing alkyl spacers of variable lenght and with different end groups can be prepared. Reaction of four equivalents of the caesium salt derived from propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside 15 with pentaerythrityltetrabromide yields the tetravalent molecule 16.

  DOI：

  10.1007/bf00811012
• 作为产物：
  描述：

  pent-4-enyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 ruthenium trichloride 、 sodium periodate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 以94%的产率得到Propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Use of n-Pentenyl Glycosides as Precursors to Various Spacer Functionalities

  摘要：

  Pent-4-enyl beta-D-glucopyranoside and its peracetylated and perbenzylated derivatives are shown to be excellent substrates for preparation of a wide variety of spacer functionalities. The spacer derivatives so obtained are promising substrates for preparing agents such as neo-glycoconjugates, micelles, and liquid crystalline phases, which are of interest for studying various biological and physiological phenomena of carbohydrates.

  DOI：

  10.1021/jo9909554

文献信息

• Saccharide derivatives and processes for their manufacture
  申请人：Ciba-Geigy Corporation

  公开号：US04873322A1

  公开（公告）日：1989-10-10

  Mono- and di-saccharidyl derivatives that are linked via a bridge member to a cephalin derivative, of the formula I, and processes for their manufacture are described. ##STR1## In the formula, R.sup.1 represents (a) aldohexosyl, (b) D-aldohexosyl that is glycosidically linked in the 4- or the 6-position to D-aldohexosyl, (c) aldopentosyl, (d) 6-deoxyaldohexosyl or (e) 2-acetylamino-2-deoxy-D-aldohexosyl, it being possible for free hydroxy groups present in the radicals mentioned under (a) to (e) above to be peracetylated, X represents oxygen or sulphur, Y represents alkylene having up to 10 carbon atoms in which from 1 to 3 non-terminal methylene groups may be replaced by oxygen, by carbonylimino or by carbonyloxy, R.sup.2 represents hydrogen, carboxy, lower alkoxycarbonyl, benzyloxycarbonyl or carbamoyl, R.sup.3 represents hydrogen and R.sup.4 represents a 1,2-dihydroxy-ethyl, 2-hydroxy-ethyl or hydroxymethyl group in which at least one hydroxy group is esterified by an unsubstituted aliphatic C.sub.10-24 -carboxylic acid and in which the other hydroxy group, if present, is free or esterified by an aliphatic C.sub.2-24 -carboxylic acid, or R.sup.3 and R.sup.4 each represents a hydroxymethyl group esterified by an unsubstituted aliphatic C.sub.10-24 -carboxylic acid. These compounds can be used as medicaments, for example for the prophylaxis and therapy of virus infections.

  本文描述了通过桥接成员连接到头孢菌素衍生物的单糖和双糖衍生物的制造方法及其公式I。##STR1##在公式中，R.sup.1代表（a）醛基己糖基，（b）D-醛基己糖基，在4-或6-位与D-醛基己糖基糖苷化，（c）醛基戊糖基，（d）6-脱氧醛基己糖基或（e）2-乙酰氨基-2-脱氧-D-醛基己糖基，上述（a）至（e）中存在的自由羟基可以被过乙酰化，X代表氧或硫，Y代表含有最多10个碳原子的烷基，其中从1到3个非末端亚甲基可以被氧、羰基亚胺或羰氧基取代，R.sup.2代表氢、羧基、低烷氧羰基、苯甲氧羰基或氨基甲酰基，R.sup.3代表氢，R.sup.4代表1,2-二羟乙基、2-羟乙基或羟甲基基团，其中至少一个羟基被未取代的脂肪族C.sub.10-24-羧酸酯化，另一个羟基（如果存在）则是自由的或被脂肪族C.sub.2-24-羧酸酯化，或者R.sup.3和R.sup.4各代表一个羟甲基基团，该基团被未取代的脂肪族C.sub.10-24-羧酸酯化。这些化合物可用作药物，例如用于病毒感染的预防和治疗。
• US4873322A
  申请人：——

  公开号：US4873322A

  公开（公告）日：1989-10-10