(2S,3R,4R,5S)-2,5-dihydroxy-1,3,4-tris(benzyloxy)-6-heptene | 180323-16-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R,4R,5S)-2,5-dihydroxy-1,3,4-tris(benzyloxy)-6-heptene
• 英文别名: (2S,3R,4R,5S)-1,3,4-tris(phenylmethoxy)hept-6-ene-2,5-diol
• CAS: 180323-16-4
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: MJZQJUWDIOVYGJ-YVHASNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S)-2,5-dihydroxy-1,3,4-tris(benzyloxy)-6-heptene 在 四氧化锇 、 N-甲基吲哚酮 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 [(2S,3S,4S,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methylsulfonyloxy-1,3,4-tris(phenylmethoxy)pentan-2-yl] methanesulfonate
  参考文献：
  名称：

  从1-木糖中合成2,5-二脱氧-2,5-亚氨基-d-甘露糖醇（DMDP）和HomoDMDP的方法

  摘要：

  描述了制备C-2取代的多羟基吡咯烷酮的简短而实用的方法。通过将格氏试剂立体选择性地添加到2,3,5-保护的醛呋喃糖中来引入C-2取代基，并通过双甲磺酰化/双亲核取代序列进行吡咯烷环系统的环化。该方法在合成HomoDMDP和DMDP中的应用证明了该方法的有效性。

  DOI：

  10.1016/j.tetlet.2007.01.125
• 作为产物：
  描述：

  (2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol 在 methanolate 、 RC₆H₄COOH 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 (2S,3R,4R,5S)-2,5-dihydroxy-1,3,4-tris(benzyloxy)-6-heptene
  参考文献：
  名称：

  衍生自δ-苄氧基醇的三氟甲磺酸酯的自发环化：高效合成C-乙烯基呋喃糖苷

  摘要：

  与三氟甲磺酸酐反应，从四-O-苄基d-hexopyranoses与[的Wittig反应得到的庚-1- enitols博士3 P  CH 2 ]铅，在一个步骤中，向3,6-脱水庚1-烯醇衍生物（“ C-乙烯基呋喃糖苷”），通过苄氧基在C-3上的参与以及伴随的脱苄基作用，以高收率获得。

  DOI：

  10.1016/0040-4039(94)02166-9

文献信息

• Synthesis and glycosidase inhibition potency of all- trans substituted 1- C -perfluoroalkyl iminosugars
  作者：Fabien Massicot、Richard Plantier-Royon、Jean-Luc Vasse、Jean-Bernard Behr

  DOI：10.1016/j.carres.2018.05.004

  日期：2018.7

  group at the pseudo-anomeric position, have been synthesized from the corresponding sugar-derived cyclic aldonitrone. The new fluorinated iminosugars as well as homoDMDP and its 6-deoxy counterpart were evaluated for their inhibitory activity against a panel of glycosidases. While the replacement of the (1',2')-dihydroxyethyl substituent of homoDMDP with -C4F9 proved detrimental for enzyme binding

  已经从相应的糖衍生的环状亚硝基硝基合成了天然存在的亚氨基糖homoDMDP的合成类似物，其在假异头位置具有全氟烷基。评价了新的氟化亚氨基糖以及homDMDP及其6-脱氧对应物对一组糖苷酶的抑制活性。尽管用-C4F9替代homoDMDP的（1'，2'）-二羟乙基取代基不利于酶结合，但引入-C3F7部分选择性地抑制了酵母对α-岩藻糖苷酶和α-葡糖苷酶的抑制活性谱。
• Synthesis of Novel Glycosidase-Inhibitory Hydroxymethyl-Substituted Polyhydroxylated Indolizidines:  Ring-Expanded Analogs of the Pyrrolizidine Alkaloids Alexine and Australine
  作者：William H. Pearson、Erik J. Hembre

  DOI：10.1021/jo960610a

  日期：1996.1.1

  The pyrrolizidine azasugars alexine (3) and australine (4) and their stereoisomers are glycosidase inhibitors of potential therapeutic use. Since the glycosidase inhibitory activity of azasugars is profoundly effected by ring size modification, the ring-expanded indolizidine analogs 7 (homoalexine), 8 (8-epihomoaustraline), 9 (homoaustraline), and 10 (8-epihomoalexine) were prepared. L-Xylose was converted into the diols 16, which were transformed into the nine-membered lactones 18 by Claisen rearrangment of the cyclic ketene acetal 17. Transesterification of the lactones to the hydroxy esters 19 followed by azide displacement and epoxidation gave the epoxides 21 and 31, Reductive double cyclization of these azido-epoxides followed by functional group adjustment provided the desired homologs 7-10. An alternative route involving stereoselective epoxidation of the nine-membered lactones was also examined. The homologs 7-10 were found to be good inhibitors of amyloglucosidase (Aspergillus niger). The inhibitory activities of 8 and 10 are comparable to those exhibited by castanospermine (5) and the pyrrolizidines alexine (3), australine (4), and 7-epiaustraline, Indolizidines 7-10 do not inhibit beta-glucosidase (almond) or alpha-glucosidase (bakers' yeast). This activity parallels that exhibited by the pyrrolizidine inhibitors alexine, australine, and 7-epiaustraline, which are generally good amyloglucosidase inhibitors but relatively weak inhibitors of alpha-glucosidase and beta-glucosidase. However, in contrast to the pyrrolizidine inhibitors which have not been reported to possess mannosidase inhibitory activity, the indolizidines 7-10 were found to inhibit alpha-mannosidase (jack bean), albeit weakly.
• Spontaneous cyclization of triflates derived from δ-benzyloxy alcohols: Efficient and general synthesis of C-vinyl furanosides
  作者：Olivier R. Martin、Feng Yang、Fang Xie

  DOI：10.1016/0040-4039(94)02166-9

  日期：1995.1

  On reaction with triflic anhydride, the hept-1-enitols resulting from the Wittig reaction of tetra-O-benzyl d-hexopyranoses with [Ph3PCH2] lead, in one step, to 3,6-anhydro-hept-1-enitol derivatives (“C-vinyl furanosides”) in high yield, by way of the participation of the benzyloxy group at C-3 with concomitant debenzylation.

  与三氟甲磺酸酐反应，从四-O-苄基d-hexopyranoses与[的Wittig反应得到的庚-1- enitols博士3 P  CH 2 ]铅，在一个步骤中，向3,6-脱水庚1-烯醇衍生物（“ C-乙烯基呋喃糖苷”），通过苄氧基在C-3上的参与以及伴随的脱苄基作用，以高收率获得。
• A concise synthesis of 2,5-dideoxy-2,5-imino-d-mannitol (DMDP) and HomoDMDP from l-xylose
  作者：Jean-Bernard Behr、Georges Guillerm

  DOI：10.1016/j.tetlet.2007.01.125

  日期：2007.3

  A short and practical procedure for the preparation of C-2 substituted polyhydroxypyrrolidines is described. The C-2 substituent is introduced by a stereoselective addition of a Grignard reagent to a 2,3,5-protected aldofuranose and the cyclization to the pyrrolidine ring system is performed through a bis-mesylation/double nucleophilic displacement sequence. The efficiency of the methodology was demonstrated

  描述了制备C-2取代的多羟基吡咯烷酮的简短而实用的方法。通过将格氏试剂立体选择性地添加到2,3,5-保护的醛呋喃糖中来引入C-2取代基，并通过双甲磺酰化/双亲核取代序列进行吡咯烷环系统的环化。该方法在合成HomoDMDP和DMDP中的应用证明了该方法的有效性。