ethyl (2R,3R)-3,4-O-isopropylidene-3,4-dihydroxy-2-methoxymethoxybutanoate | 287119-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2R,3R)-3,4-O-isopropylidene-3,4-dihydroxy-2-methoxymethoxybutanoate
• 英文别名: ethyl 3,4-O-isopropylidene-2-O-(methoxymethyl)-D-erythronate
• CAS: 287119-14-6
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: MPVFBLDQKGHKIQ-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl (2R,3R)-3,4-O-isopropylidene-3,4-dihydroxy-2-methoxymethoxybutanoate 在 吡啶 、 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 15.0h， 生成 (2R,3S)-3-(2-nitroimidazol-1-ylmethoxy)-1,2,4-tribenzoyloxybutane
  参考文献：
  名称：

  JP6071715

  摘要：

  公开号：
• 作为产物：
  描述：

  ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以87%的产率得到ethyl (2R,3R)-3,4-O-isopropylidene-3,4-dihydroxy-2-methoxymethoxybutanoate
  参考文献：
  名称：

  Enantioselective Synthesis of Ethyl 4,5,7,8,9-Penta-O-acetyl-2,6-anhydro- 3-deoxy-D-erythro-L-gluca-nononate: a 2-Monodeoxygenated Derivative of `2-Keto-3-deoxy-D-glycero-D-galacto-nononic Acid'

  摘要：

  A study aimed at developing an enantioselective synthesis of the title compound 23, a 2-monodeoxy analogue of;he naturally occurring (+)-2-keto-3-deoxy-D-glycero-D-galacto-2-nononic acid (KDN),is reported. From D-mannose as starting material, the chiral 1,3-diene 10, activated by a silyloxy substituent at C(2), was prepared in six steps (Scheme I). However, the intermediates were often contaminated with varying amounts of by-products arising from overoxidation during cleavage with periodic acid. An alternative route starting from the inexpensive and readily available D-isoascorbic acid (12), though a little longer than the first, satisfactorily circumvented the purification problem and led to the desired dienes 17 in good yields (scheme2). The [Co-II(S.S)-(+)-salen]-catalyzed hetero-Diels-Alder reactions of the aforementioned dienes with ethyl glyoxylate proceeded smoothly at room temperature, giving the dihydropyrano adducts 18 in moderate yields (Scheme 3). Dihydroxylation of 18a followed by reduction of the keto function gave the desired 4,5-trans dihydroxy moiety of the KDN framework (Scheme 4, see 21). The spectroscopic data of the penta-O-acetylated 2-deoxy-KDN ethyl ester 23 were consistent with those reported for the corresponding methyl ester derived from natural KDN.

  DOI：

  10.1002/(sici)1522-2675(20000510)83:5<943::aid-hlca943>3.0.co;2-h

文献信息

• A ‘Chiron’ approach to novel phytosphingosine mimetics based on a cascade [3,3]-sigmatropic rearrangement
  作者：Jana Špaková Raschmanová、Simona Fazekašová、Miroslava Martinková、Martin Fábian、Martina Bago Pilátová、Josef Cvačka、Edita Kofroňová、Roman Mezencev

  DOI：10.1016/j.carres.2024.109158

  日期：2024.7

  Straightforward access to enantiomerically pure 3,4-diamino-3,4-dideoxyphytosphingosines, as novel analogues of natural --phytosphingosine was accomplished, starting from two available chirons: dimethyl -tartrate and -isoascorbic acid. A sequential Overman rearrangement followed by late-stage introduction of the alkyl side chain moiety via olefin cross-metathesis is the cornerstone of this approach

  从两种可用的嵌合体：酒石酸二甲酯和异抗坏血酸开始，可以直接获得对映体纯的 3,4-二氨基-3,4-二脱氧植物鞘氨醇，作为天然植物鞘氨醇的新型类似物。连续的 Overman 重排，然后通过烯烃交叉复分解在后期引入烷基侧链部分，是该方法的基石。基于其抑制人类癌细胞增殖的能力，对合成的鞘氨醇模拟物进行了初步评估研究，结果表明 (2,3,4)-2,3,4-triaminooctadecan-1-ol 对 Jurkat 和 HeLa 细胞具有良好的细胞毒性三盐酸盐。
• JP6082644
  申请人：——

  公开号：——

  公开（公告）日：——