methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate | 2880-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate
• 英文别名: methyl (4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxane-2-carboxylate
• CAS: 2880-95-7
• 化学式: C₉H₁₆O₇
• 分子量: 236.222
• InChiKey: PUXQJBPBWGJAMX-JBPTWFHOSA-N

物化性质

• 沸点：
  385.4±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 生成 methyl (methyl 3-deoxy-7-bromo-D-arabino-heptulopyranosid)oate
  参考文献：
  名称：

  Construction of an enzyme-targeted organophosphonate using immobilized enzyme and whole-cell synthesis

  摘要：

  DOI：

  10.1021/ja00285a022
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 盐酸 、 硫酸 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate
  参考文献：
  名称：

  Construction of an enzyme-targeted organophosphonate using immobilized enzyme and whole-cell synthesis

  摘要：

  DOI：

  10.1021/ja00285a022

文献信息

• The first synthesis of the ketene dithioacetals from sugar lactones: a convenient access to 3-ulosonic acids
  作者：Jacek Młynarski、Anna Banaszek

  DOI：10.1016/s0040-4039(98)01045-4

  日期：1998.7

  Isomeric 2-deoxy aldonolactones undergo Horner-Emmons reactions with 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]1,3-dithiane, to give the corresponding ketene dithioacetals, which are the key intermediates in the synthesis of 3-deoxy-2-keto-aldonic acids.

  异构的2-脱氧醛内酯与2- [双（2,2,2-三氟乙氧基）磷酰基] 1,3-二硫杂环丁烷进行霍纳-埃蒙反应，得到相应的烯酮二硫缩醛，它们是合成3-的关键中间体脱氧-2-酮-醛糖酸。
• Synthesis of 4-amino 3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate, the biosynthetic precursor of C7N units in ansamycin antibiotics
  作者：Andreas Kirschning、Philippe Bergon、Jeh-Jeng Wang、Steven Breazeale、Heinz G. Floss

  DOI：10.1016/0008-6215(94)84211-6

  日期：1994.4

  Abstract The synthesis of 4-amino-3,4-dideoxy- d -arabino-heptulosonic acid 7-phosphate (15), the first committed intermediate in a new branch of the shikimate pathway of aromatic biosynthesis, is reported from 2-deoxy- d -glucose in 14 steps in 10–12% overall yield.

  摘要据报道，由2-脱氧-苯甲基合成了4-氨基-3,4-二脱氧-d-阿拉伯庚酸七磷酸酯（15），这是芳香族生物合成the草酸途径新分支中的第一个固定中间体。 d-葡萄糖分14步产生，总产率为10–12％。
• Convenient preparation of α- and β-glycosides of novel isomeric 3-deoxy-hept-2-ulosaric acids diesters
  作者：Jacek Mlynarski、Anna Banaszek

  DOI：10.1016/s0040-4020(97)00675-3

  日期：1997.7

  d-lyxo-hept-2-ulosonic acids were obtained from the individual α and β anomers of the same methyl (methyl 3-deoxy-d-arabino-hept-2-ulopyranosid)-onate in a sequential epimerisation at C-4 and/or C-5 of their appropriate O-trifluoromethanesulfonic derivatives, using cesium acetate. Subsequent oxidation of the 7-OH group in these compounds lead to the new isomeric 3-deoxy-hept-2-ulosaric acids derivatives.

  甲基-3-脱氧α和β-D-核糖，D-来苏-庚-2- ulosonic酸从个体α和相同的甲基端基异构体β（得到3-脱氧-D-阿拉伯-庚-2- ulopyranosid）-onate以顺序的差向异构化在C-4和/或C-5及其相应的ø -三氟甲衍生物，使用乙酸铯。这些化合物中的7-OH基团随后被氧化，生成了新的异构体3-脱氧-庚-2-缩醛酸衍生物。
• Synthesis of 3-deoxy-d-arabino-2-heptulosonic acid 7-phosphate by phosphorylation of methyl (methyl 3-deoxy-d-arabino-heptulopyranosid)onate
  作者：Mella Adlersberg、David B. Sprinson

  DOI：10.1016/0008-6215(84)85101-0

  日期：1984.4

  Abstract 3-Deoxy- d - arabino -2-heptulosonic acid 7-phosphate ( 5 ), the first committed intermediate in aromatic amino acid biosynthesis, has been synthesized in good yield by treatment of methyl (methyl 3-deoxy- d - arabino -2-heptulopyranosid)onate with diphenylphosphoric chloride under mild conditions to give the 7-diphenyl phosphate. Catalytic removal of the phenyl residues, followed by base-catalyzed

  摘要3-甲基3-甲基（脱氧-d-阿拉伯糖-在温和的条件下，用二苯基氯化磷与2-庚基吡喃二酮基磺酸盐生成7-二苯基磷酸酯。催化除去苯基残基，然后进行碱催化水解，导致形成（甲基3-脱氧-d-阿拉伯--2-庚基吡喃糖苷）膦酸二氢7-磷酸酯（4），生成结晶的三（环己基）铵盐。酸催化4水解，得到5，用于纯化3-脱氢奎宁合成酶。
• Formation of 3-amino-5-hydroxybenzoic acid, the precursor of mC7N units in ansamycin antibiotics, by a new variant of the shikimate pathway
  作者：C. G. Kim、A. Kirschning、P. Bergon、Y. Ahn、J. J. Wang、M. Shibuya、H. G. Floss

  DOI：10.1021/ja00038a090

  日期：1992.6