1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosiduronamide | 156325-49-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosiduronamide
• 英文别名: 1,2-isopropylidene-5-O-allyl-α-D-glucofuranosiduronamide；(2S)-2-[(3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-prop-2-enoxyacetamide
• CAS: 156325-49-4
• 化学式: C₁₂H₁₉NO₆
• 分子量: 273.286
• InChiKey: LLSXPILEDQHXLG-ZCLKDUABSA-N

物化性质

• 沸点：
  478.6±45.0 °C(predicted)
• 密度：
  1.248±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  100
• 氢给体数：
  2
• 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-glucofuranosiduronamide 在 三乙胺 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 Dowex 50 W X₂ (H⁺ form) 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 9.17h， 生成 Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide
  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 在 氨 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosiduronamide
  参考文献：
  名称：

  Structural analogues of the antibiotic moenomycin a with a D-glucose-derived unit F

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)85066-3

文献信息

• 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.
• 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.