5,6-O-isopropylidene-L-galactonic acid γ-lactone | 69602-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-O-isopropylidene-L-galactonic acid γ-lactone
• 英文别名: 5,6-O-isopropylidene-L-galactono-1,4-lactone；(3S,4S,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one
• CAS: 69602-93-3
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: JNTPPVKRHGNFKM-ZTYPAOSTSA-N

物化性质

• 沸点：
  355.7±42.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-O-isopropylidene-L-galactonic acid γ-lactone 在 吡啶 、 sodium azide 、 四丁基碘化铵 、 二正丁基氧化锡 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.0h， 生成 5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-altrono-γ-lactone
  参考文献：
  名称：

  所有八种立体异构体D-glyconic-delta-lactams：合成，构象分析和评估，均作为糖苷酶抑制剂。

  摘要：

  已经开发了一种有效且通用的合成途径，用于合成所有八种立体异构D-糖基-δ-内酰胺。该策略包括作为关键步骤的立体发散性δ-内酰胺的形成，其具有构型保留或在起始C-内酰胺的C-4处反转，以从一个母体γ-内酯产生两种δ-内酰胺差向异构体。通过X射线晶体学分析和分子模型检查了八个糖基-δ-内酰胺的构象。构象和糖苷酶抑制分析为设计新型糖苷酶抑制剂提供了有用的信息。

  DOI：

  10.1021/jo000141j
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 半乳糖酸內酯 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 以92%的产率得到5,6-O-isopropylidene-L-galactonic acid γ-lactone
  参考文献：
  名称：

  Asymmetric synthesis of the new marine epoxy lipid, (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol

  摘要：

  An efficient and stereocontrolled process is described for the preparation of (6S, 7S, 9S, 10S)-6,9-epoxynonadee-18-ene-7.10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala. The key 2,3,5-trisubstituted tetrahydrofuran ring was constructed by stereoselective hydrogenation of the hemiketal derivative elaborated through nucleophilic addition of Grignard reagent in the presence of CeCl3 to the highly functionalized lactone derived from L-galactono-1,4-lactone,4-lactone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00244-0

文献信息

• Flexible Synthesis and Biological Activity of Uronic Acid-Type <i>gem</i>-Diamine 1-<i>N</i>-Iminosugars:  A New Family of Glycosidase Inhibitors
  作者：Yoshio Nishimura、Eiki Shitara、Hayamitsu Adachi、Minako Toyoshima、Motowo Nakajima、Yoshiro Okami、Tomio Takeuchi

  DOI：10.1021/jo982448c

  日期：2000.1.1

  An efficient and flexible synthetic route to four gem-diamine 1-N-iminosugars of uronic acid-type (D-glucuronic, D-mannuronic, L-iduronic, and L-guluronic acid), a new family of glycosidase inhibitor, from l-galactono-1,4-lactone have been developed in an enantiodivergent fashion through a sequence involving as the key steps (a) the formation of gem-diamine 1-N-iminopyranose ring by the Mitsunobu reaction

  一种高效灵活的合成路线，可合成四种糖醛酸酶抑制剂家族的四个糖醛酸类型的宝石-二胺1-N-亚氨基糖（D-葡萄糖醛酸，D-甘露糖醛酸，L-异戊糖醛酸和L-古洛糖醛酸） -半乳糖-1,4-内酯的开发通过对映异构的方式进行，其顺序涉及以下关键步骤：（a）通过胺的Mitsunobu反应形成宝石二胺1-N-亚氨基吡喃糖环，以及（b）通过酮的Wittig反应，硼氢化和氧化以及Sharpless氧化引入羧酸基团。D-葡萄糖醛酸和D-甘露糖醛酸型1-N-亚氨基糖（3S，4R，5R，6R）-和（3S，4R，5R，6S）-4，5-二羟基-6-三氟乙酰氨基-3-哌啶羧酸酸被证明是β-D-葡萄糖醛酸苷酶的有效抑制剂（IC（50）6。
• Method of preparing ascorbic acid and intermediates specially adapted for use therein
  申请人：PFIZER INC.

  公开号：EP0000092A1

  公开（公告）日：1978-12-20

  The invention relates to a process for preparing ascorbic acid in which (a) gulono-, galactono-, idono- or talono-1,4- lactone is reacted with at least one hydroxyl-protecting reagent so as to protected the free hydroxyl groups in the 5-, 6-and either the 2- or 3- positions, or, reacting gulono- or idono-1,4-lactone with at least one hydroxyl-protecting reagent so as to protect the free hydroxyl groups in the 3-, 5- and optionally the 6- positions (b) oxidizing the free hydroxyl group at the 2- or 3- position to oxidize it to an oxo group and (c) hydrolyzing the compound formed in (b) to ascorbic acid. Certain novel intermediates useful in the above process are also covered.

  本发明涉及一种制备抗坏血酸的工艺，在该工艺中，(a)古洛内酯、半乳糖内酯、伊东内酯或 Talono-1,4- 内酯与至少一种羟基保护试剂反应，以保护 5-、6-和 2 或 3-位上的游离羟基，或者，古洛内酯或伊东内酯与至少一种羟基保护试剂反应，以保护 3-、5-和可选的 6-位上的游离羟基 (b)氧化游离羟基以制备抗坏血酸、4-内酯与至少一种羟基保护试剂反应，以保护 3-、5-和任选 6-位上的游离羟基 (b) 氧化 2-或 3-位上的游离羟基，使其氧化为氧代基团，以及 (c) 将 (b) 中形成的化合物水解为抗坏血酸。此外，还介绍了在上述工艺中有用的某些新型中间体。
• Straightforward synthesis of derivatives of d- and l-galactonic acids as precursors of stereoregular polymers
  作者：Carmen L. Romero Zaliz、Oscar Varela

  DOI：10.1016/s0957-4166(03)00588-3

  日期：2003.9

  High yielding routes for the synthesis of selectively protected derivatives Of D- and L-galactonic acids. having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono- 1.4-lactones was developed as a key step of the sequence. For example. 6-azido-6-deoxy-L-galactono- 1.4-lactone 16 was converted into the potassium salt and methylated (NaH, DMSO, Mel) to the methyl ester of the 2,3.4,5-tetra-O-methyl derivative 12. Compound 16 was readily prepared by bromination at C-6 Of L-galactonolactone 1 and isopropylidenation followed by substitution of bromine by azide and removal of the protecting groups. Hydrolysis of the methyl ester of 12 and hydrogenation of the azide led to the tetra-O-methyl derivative of the 6-amino acid 18 with 52% overall yield from 1. The same sequence applied to D-galactonolactone 19 led to the enantiomeric amino acid 25 with a 47% overall yield. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of di-O-isopropylidene derivatives of L-fructose
  作者：Svein Morgenlie

  DOI：10.1016/s0008-6215(00)80782-x

  日期：1982.9
• US4111958A
  申请人：——

  公开号：US4111958A

  公开（公告）日：1978-09-05