forosamine | 56587-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: forosamine
• 英文别名: D-forosamine；(5S,6R)-5-(dimethylamino)-6-methyloxan-2-ol
• CAS: 56587-30-5；56587-32-7；90227-41-1
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: OSOMGRACWFYJNS-KVARREAHSA-N

物化性质

• 沸点：
  240.4±40.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  forosamine 、 在 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以45%的产率得到
  参考文献：
  名称：

  Natural Product Disaccharide Engineering through Tandem Glycosyltransferase Catalysis Reversibility and Neoglycosylation

  摘要：

  A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, the chemoenzymatic method presented is expected to be broadly applicable.

  DOI：

  10.1021/ol3023374
• 作为产物：
  描述：

  spiramycin 在 盐酸 、 水 作用下， 反应 16.0h， 以87%的产率得到forosamine
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Doxycycline Neoglycosides

  摘要：

  A set of 37 doxycycline neoglycosides were prepared, mediated via a C-9 alkoxyamino-glycyl-based spacer reminiscent of that of tigecycline. Subsequent in vitro antibacterial assays against representative drug-resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2'-amino-alpha-D-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strain E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two-step strategy anticipated to be broadly applicable for neoglycorandomization.

  DOI：

  10.1021/np4003096

文献信息

• Chemoenzymatic Synthesis of Spinosyn A
  作者：Hak Joong Kim、Sei-hyun Choi、Byung-sun Jeon、Namho Kim、Rongson Pongdee、Qingquan Wu、Hung-wen Liu

  DOI：10.1002/anie.201407806

  日期：2014.12.1

  significantly elevated level of structural complexity that renders the chemical synthesis of these natural products challenging. We report herein a total synthesis of the widely used polyketide insecticide spinosyn A by exploiting the prowess of both chemical and enzymatic methods. As more polyketide biosynthetic pathways are characterized, this chemoenzymatic approach is expected to become readily adaptable

  通过聚酮合酶 (PKS) 生物合成聚酮主链后，PKS 后修饰会导致结构复杂性显着升高，从而使这些天然产物的化学合成变得具有挑战性。我们在此报道了通过利用化学和酶促方法的优势，全合成了广泛使用的聚酮化合物杀虫剂多杀菌素A。随着更多聚酮化合物生物合成途径的表征，这种化学酶方法预计将很容易适应通过更精细的 PKS 后修饰来简化其他复杂聚酮化合物的合成。
• PESTICIDAL COMPOSITIONS
  申请人：Crouse Gary D.

  公开号：US20090209476A1

  公开（公告）日：2009-08-20

  The invention disclosed in this document is related to the field of pesticides and their use in controlling pests. A compound having the following structure is disclosed.

  这份文件中披露的发明涉及杀虫剂领域及其在控制害虫方面的应用。披露了一种具有以下结构的化合物。
• Voelter, Wolfgang; Malik, Abdul; Afza, Nighat, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 3, p. 405 - 406
  作者：Voelter, Wolfgang、Malik, Abdul、Afza, Nighat

  DOI：——

  日期：——
• Dyong,I. et al., Chemische Berichte, 1978, vol. 111, p. 559 - 565
  作者：Dyong,I. et al.

  DOI：——

  日期：——
• US8178658B2
  申请人：——

  公开号：US8178658B2

  公开（公告）日：2012-05-15