1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosidurono-6,3-lactone | 126214-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosidurono-6,3-lactone
• 英文别名: (1S,2R,6R,8S,9S)-4,4-dimethyl-9-prop-2-enoxy-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-10-one
• CAS: 126214-82-2
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: UDIVOIKURXEERV-HTFKAIDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosidurono-6,3-lactone 在 四(三苯基膦)钯 、 三乙胺 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 Dowex 50 W X₂ (H⁺ form) 、 氨 、 水 、 三正丁基氢锡 、 乙酸肼 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 溶剂黄146 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 104.01h， 生成 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-1-O-{[(R)-2-methoxycarbonyl-2-(hexyloxy)-ethoxy]-(2,2,2-trichloro-1,1-dimethylethoxy)-phosphoryl}-α-D-glucopyranuronamide
  参考文献：
  名称：

  Moenomycin A: The role of the methyl group in the moenuronamide unit and a general discussion of structure-activity relationships

  摘要：

  Two disaccharide analogues 1b and 17a of moenomycin A have been synthesized and their antibiotic and transglycosylase-inhibiting properties have been determined. The results permit for the first time to arrive at a general view of the structural requirements in this class of compounds necessary to elicit antibiotic activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01063-1
• 作为产物：
  描述：

  D-glucurono-3,6-lactone acetonide 生成 1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosidurono-6,3-lactone
  参考文献：
  名称：

  WESSEL, HANS PETER, J. CARBOHYDR. CHEM., 8,(1989) N, C. 443-455

  摘要：

  DOI：

文献信息

• Studies on the Synthesis of Trisaccharide Analogues of the Antibiotic Moenomycin A
  作者：Guangbin Yang、Lothar Hennig、Matthias Findeisen、Ramona Oehme、Sabine Giesa、Peter Welzel

  DOI：10.1002/hlca.200490160

  日期：2004.7

  A new approach for the synthesis of moenomycin trisaccharide analogues is reported in which three monosaccharide building blocks are used and allows the introduction of different substituents at the 6-position of unit E (Scheme 2). Furthermore, a new procedure for the introduction and manipulation of unit F is described (Scheme 3).

  报道了一种合成莫能霉素三糖类似物的新方法，其中使用了三个单糖结构单元，并允许在单元E的6-位引入不同的取代基（方案2）。此外，描述了用于引入和操纵单元F的新过程（方案3）。
• Structural analogues of the antibiotic moenomycin a with a D-glucose-derived unit F
  作者：Monika Heuer、Karsten Hohgardt、Frauke Heinemann、Harald Kühne、Wolfgang Dietrich、Detlef Grzelak、Dietrich Müller、Peter Welzel、Astrid Markus、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/s0040-4020(01)85066-3

  日期：1994.2

  Disaccharide derivative 1a is the smallest transglycosylase inhibiting compound known up to now. Structurally closely related compounds 11b and 19c have been synthesized. They do not inhibit the transglycosylase demonstrating the high specificity of the interaction between inhibitor 1a and the binding-site at the enzyme.
• WESSEL, HANS PETER, J. CARBOHYDR. CHEM., 8,(1989) N, C. 443-455
  作者：WESSEL, HANS PETER

  DOI：——

  日期：——
• Moenomycin A: The role of the methyl group in the moenuronamide unit and a general discussion of structure-activity relationships
  作者：Naser El-Abadla、Maxime Lampilas、Lothar Hennig、Matthias Findeisen、Peter Welzel、Dietrich Müller、Astrid Markus、Jean van Heijenoort

  DOI：10.1016/s0040-4020(98)01063-1

  日期：1999.1

  Two disaccharide analogues 1b and 17a of moenomycin A have been synthesized and their antibiotic and transglycosylase-inhibiting properties have been determined. The results permit for the first time to arrive at a general view of the structural requirements in this class of compounds necessary to elicit antibiotic activity. (C) 1998 Elsevier Science Ltd. All rights reserved.