1-O-(1-carboxylbutyl-4-oxyl) 2,3,4-tri-O-acetyl-β-L-fucopyranoside | 116112-86-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 1-O-(1-carboxylbutyl-4-oxyl) 2,3,4-tri-O-acetyl-β-L-fucopyranoside
• 英文别名: 4-(2,3,4-tri-O-acetyl-β-L-fucopyranosyloxy)butyric acid；4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxybutanoic acid
• CAS: 116112-86-8
• 化学式: C₁₆H₂₄O₁₀
• 分子量: 376.361
• InChiKey: GQADIPJUYVOKAM-CRLRYRHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-O-(1-carboxylbutyl-4-oxyl) 2,3,4-tri-O-acetyl-β-L-fucopyranoside 在 重氮甲烷 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 3-(Methoxycarbonyl)propyl 2,3,4-tri-O-acetyl-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates

  摘要：

  Omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C-7, C-9, C-12, and C-15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C-7 and C-9 carbon chains. D-xylose and 2-acetamido-2-deoxy-L-fucose having a C-9 carbon chian, and 9-(methoxycarbonyl)-3,6-dioxanoyl glycopyranosides of D-mannose. 2-acetamido-2-deoxy-D-mannose, and L-fucose were' synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-ManNAc-(1 --> 2)-alpha-D-Man, beta-D-GlcNAc-(1 --> 2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-ManNAc-(1 --> 6)-alpha-D-Man, and beta-D-GlcNAc-(1 --> 6)-alpha-D-Man, were also synthesized.

  DOI：

  10.1016/s0008-6215(00)90517-2
• 作为产物：
  描述：

  1-O-(4-pentenyl) 2,3,4-tri-O-acetyl-β-L-fucopyranoside 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 以100%的产率得到1-O-(1-carboxylbutyl-4-oxyl) 2,3,4-tri-O-acetyl-β-L-fucopyranoside
  参考文献：
  名称：

  Design and Synthesis of Peptide Mimetics of GDP-Fucose: Targeting Inhibitors of Fucosyltransferases

  摘要：

  基于UDP-N-乙酰葡糖胺的多肽模拟物尼克霉素Z对N-乙酰葡糖胺转移酶具有强效抑制活性的背景，我们设计并合成了新型的GDP-岩藻糖多肽模拟物，其目标是抑制从GDP-岩藻糖转移l-岩藻糖至寡糖的岩藻糖转移酶。GDP-岩藻糖模拟物的合成路线是利用 l-苏氨酸醛缩酶催化的酶促醛缩反应来制备携带δ-²-羟基-δ±-l-氨基酸的鸟嘌呤，这是一种关键的合成中间体。

  DOI：

  10.1055/s-2003-44984

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.

  本发明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备方法。公式I如下：##STR1##在公式中，R.sup.1代表(a)醛基己糖基，(b)在4-或6-位与D-醛基己糖基糖苷化的D-醛基己糖基，(c)醛基戊糖基，(d)6-去氧醛基己糖基或(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代表碳原子数为1至3的非末端亚甲基可以被氧、羰基亚胺或羰氧基替代的长度为10的烷基，R.sup.2代表氢、羧基、低碳基氧羰基、苄氧基羰基或氨基甲酰基，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，如果存在另一个羟基，则该羟基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。这些化合物可以用作药物，例如用于预防和治疗病毒感染。
• US4873322A
  申请人：——

  公开号：US4873322A

  公开（公告）日：1989-10-10