allyl (3,4-O-isopropylidene-α-D-galactopyranosid)uronamide | 142543-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: allyl (3,4-O-isopropylidene-α-D-galactopyranosid)uronamide
• 英文别名: (3aR,4S,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-6-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-carboxamide
• CAS: 142543-98-4
• 化学式: C₁₂H₁₉NO₆
• 分子量: 273.286
• InChiKey: OBYAXVVISNVYKV-CDDJKKQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 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：

  allyl (3,4-O-isopropylidene-α-D-galactopyranosid)uronamide 在 camphor-10-sulfonic acid 甲醇 、 溶剂黄146 、 三丁基氧化锡 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 42.5h， 生成 allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-α-D-galactopyranosiduronamide
  参考文献：
  名称：

  Moenomycin A-Moenomycin A最小的抗生素活性降解产物的D-半乳糖醛酰胺类似物的构效关系合成

  摘要：

  合成了化合物10c，它是2的半乳糖醛酰胺类似物，这是具有完全抗生素活性的莫诺霉素A（1）的最小降解产物。10c没有抗生素活性。

  DOI：

  10.1016/s0040-4020(01)80351-3
• 作为产物：
  描述：

  allyl (allyl α-D-galactopyranosid)uronate 在 对甲苯磺酸 氨 作用下， 以 甲醇 为溶剂， 反应 24.75h， 生成 allyl (3,4-O-isopropylidene-α-D-galactopyranosid)uronamide
  参考文献：
  名称：

  Moenomycin A-Moenomycin A最小的抗生素活性降解产物的D-半乳糖醛酰胺类似物的构效关系合成

  摘要：

  合成了化合物10c，它是2的半乳糖醛酰胺类似物，这是具有完全抗生素活性的莫诺霉素A（1）的最小降解产物。10c没有抗生素活性。

  DOI：

  10.1016/s0040-4020(01)80351-3

文献信息

• A new method for the cleavage of allyl glycosides
  作者：Joachim Lüning、Uwe Möller、Norbert Debski、Peter Welzel

  DOI：10.1016/s0040-4039(00)73801-9

  日期：1993.9

  Allyl glycosides can be cleaved by Wacker oxidation followed by photolysis in the presence of triethylamine.

  烯丙基糖苷可通过Wacker氧化裂解，然后在三乙胺存在下进行光解。
• The first synthesis of a moenomycin-type transglycosylase inhibitor
  作者：Joachim Lüning、Uwe Möller、Dietrich Müller、Peter Welzel、Astrid Markus、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/s0040-4020(01)81550-7

  日期：1993.1

  Starting from chitobiose octaacetate, D-galacturonic acid derivative 3, and D-glyceric acid derived building block 7, the moenomycin trisaccharide analogue 8c has been synthesized. 8c is an as active transglycosylase inhibitor as moenomycin A.
• A chemoenzymatic approach towards moenomycin structural analogues
  作者：Gerhard Range、Ralf Krähmer、Peter Welzel、Dietrich Müller、Guido F. Herrmann、Udo Kragl、Christian Wandrey、Astrid Markus、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/s0040-4020(96)01116-7

  日期：1997.2

  The trisaccharide moenomycin analogue 1c has been synthesized. One starting material was N-acetyllactosamine obtained by an enzyme-catalyzed transglycosylation. 1c differs from moenomycin degradation product 1a only in two positions of unit C. In contrast to 1a the synthetic 1c is antibiotically inactive. (C) 1997, Elsevier Science Ltd.
• The first moenomycin antibiotic without the methyl-branched uronic acid constituent.- Unexpected structure activity relations
  作者：Martina Heßler-Klintz、Kurt Hobert、Armin Biallaß、Torsten Siegels、Monika Hiegemann、Armin Maulshagen、Dietrich Müller、Peter Welzel、Gerhard Huber、Dirk Böttger、Astrid Markus、Gerhard Seibert、Andreas Stärk、Hans-Wolfram Fehlhaber、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/s0040-4020(01)87242-2

  日期：1993.8

  Isolation and structure elucidation of a new moenomycin antibiotic (C1, 1e) that lacks the branching methyl group in the 4-position of unit F are reported. The smallest antibiotically active degradation product of le is the trisaccharide derivative 3. This observation is in contrast to structure activity relations in the moenomycin A series where it was found that disaccharide 4a is fully active.
• Glycosylations with tetra-O-acetyl-N-allyloxycarbonylamino-2-deoxy-β-D-glucose in polar solvents
  作者：Frauke Heinemann、Monika Hiegemann、Peter Welzel

  DOI：10.1016/s0040-4020(01)92269-0

  日期：——

  Glycosylations with the title compound were performed in dimethylformamide, acetonitrile, and nitromethane. The latter solvent was found to give good results whereas DMF caused 1-O-deacetylation.