4-O-mesyl-6-O-benzyl-D-gulal | 792908-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-mesyl-6-O-benzyl-D-gulal
• 英文别名: [(2R,3R,4S)-4-hydroxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl] methanesulfonate
• CAS: 792908-47-5
• 化学式: C₁₄H₁₈O₆S
• 分子量: 314.359
• InChiKey: AVXNZHGEUGJKSN-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-O-mesyl-6-O-benzyl-D-gulal 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 0.25h， 生成 (1S,2R,6S)-2-Benzyloxymethyl-3,7-dioxa-bicyclo[4.1.0]hept-4-ene
  参考文献：
  名称：

  钯催化的 D-Glucal 衍生的 β-和 α-乙烯基环氧乙烷的改进的区域选择性和立体选择性 O-糖基化

  摘要：

  D-葡萄糖衍生的乙烯基环氧乙烷作为优异的糖基供体的 Pd0 催化糖基化已经以区域和立体选择性方式完成。各种糖基受体与乙烯基环氧乙烷 1a 和 1b 反应后，在五分钟内以良好到极好的收率产生相应的 2,3-不饱和 O-糖苷。上述反应也已用于合成 2,3-不饱和三糖，它们是完全氧化、脱氧和双脱氧糖的潜在前体。

  DOI：

  10.1002/ejoc.201200242
• 作为产物：
  描述：

  3-O-(t-butyldimethylsilyl)-6-O-benzyl-D-gulal 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.33h， 生成 4-O-mesyl-6-O-benzyl-D-gulal
  参考文献：
  名称：

  立体有择非催化α- ö -Glycosylation和α- Ç借助于-Glycosidation一个新的d Gulal源性α乙烯基环氧乙烷

  摘要：

  通过新途径制得的通往d-古拉尔系统的α-乙烯基环氧乙烷5与O-亲核试剂（醇和二-O-异亚丙基-α - d-单糖）和C-亲核试剂（烷基锂）反应，得到一个完全立体选择性方式，相应的2-不饱和的α ø -和ç -glycosides具有相同的结构的起始环氧化物。

  DOI：

  10.1021/jo0491152

文献信息

• Synthesis of diastereoisomeric 6-deoxy-d-allal- and 6-deoxy-d-galactal-derived allyl epoxides and examination of the regio- and stereoselectivity in nucleophilic addition reactions. Comparison with the corresponding 6-O-functionalized allyl epoxides
  作者：Valeria Di Bussolo、Lucilla Favero、Maria Rosaria Romano、Mauro Pineschi、Paolo Crotti

  DOI：10.1016/j.tet.2008.06.039

  日期：2008.8

  6-deoxy-d-allal- and 6-deoxy-d-galactal-derived allyl epoxides 8α and 8β have been stereoselectively prepared and their behaviour as glycosyl donors in addition reactions with nucleophiles examined and compared with that of the corresponding 6-OR (R=Bn, Tr) substituted epoxides. The completely stereoselective substrate-dependent glycosylation process found in the reaction of 8α and 8β with O-nucleophiles (alcohols

  新的6-脱氧d-allal-和6-脱氧d半乳醛衍生的环氧化物烯丙基8α和8β已立体选择性地制备，并且检查，并与相应的比较它们在与亲核试剂加成反应的糖基供体行为6- OR（R = Bn，Tr）取代的环氧化物。完全立体选择性衬底依赖性糖基化方法中的反应中发现8α和8β与ö -nucleophiles（醇类和部分保护的单糖）和Ç -nucleophiles（烷基锂化合物和TMSCN），表明了6 OR基团在侧链中确定选择性不是必需的。8α和8β的反应与叠氮化物（TMSN 3，N-亲核试剂）的结合使得有可能修改先前提出的形成相应的顺式叠氮基醇（顺式-1，2-加成产物）的合理性。
• Enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans from d-allal- and d-galactal-derived vinyl epoxides
  作者：Valeria Di Bussolo、Salvatore Princiotto、Vittorio Bordoni、Elisa Martinelli、Lucilla Favero、Stefano Crotti、Gloria Uccello Barretta、Federica Balzano、Mauro Pineschi、Paolo Crotti

  DOI：10.1016/j.tet.2019.06.003

  日期：2019.8

  Upon treatment with the metal enolates of methylene active compounds (dimethyl malonate and dibenzoylmethane) (C-nucleophiles) and benzyl carbamate (N-nucleophile), d-allal- and d-galactal-derived vinyl epoxides are stereoselectively transformed, in a single step, into diastereoisomeric, highly functionalized, enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans.

  用亚甲基活性化合物（丙二酸二甲酯和二苯甲酰甲烷）（C-亲核试剂）和氨基甲酸苄酯（N-亲核试剂）的金属烯醇盐处理后，只需一步即可立体选择性地转化衍生自d-铝和d-半乳糖的乙烯基环氧化物。分为非对映异构，高度官能化，对映纯的顺式和反式-2,5-二取代-2,5-二氢呋喃。
• Stereoselective Uncatalyzed Synthesis of 2,3-Unsaturated-4-N-substituted-β-<i>O</i>-glycosides by Means of a New <scp>d</scp>-Galactal-Derived <i>N</i>-(Mesyl)-aziridine
  作者：Valeria Di Bussolo、Maria Rosaria Romano、Lucilla Favero、Mauro Pineschi、Paolo Crotti

  DOI：10.1021/jo051877p

  日期：2006.2.1

  The reaction of the new (D)-galactal-derived allylic aziridine 1 beta with O-nucleophiles (alcohols and monosaccharides) affords, in a high to complete beta-stereoselectivity, the corresponding 2,3-unsaturated-beta-O-glycosides bearing a beta-N-functionality at C(4).
• Aminolysis of glycal-derived allyl epoxides and activated aziridines. Effects of the absence of coordination processes on the regio- and stereoselectivity
  作者：Valeria Di Bussolo、Lorenzo Checchia、Maria Rosaria Romano、Lucilla Favero、Mauro Pineschi、Paolo Crotti

  DOI：10.1016/j.tet.2009.11.059

  日期：2010.1

  The addition of primary and secondary aliphatic amines to glycal-derived allyl epoxides is completely 1,2-regio- and anti-stereoselective, whereas mixtures of the corresponding anti-1,2- [3-N-(substituted-amino) glycals] and anti-1,4-addition products (N-glycosyl amines) are obtained with N-(mesyl)-aziridines. In this way, structural moieties, otherwise difficult to synthesize, are obtained by means of a very simple protocol. The regio- and stereoselectivity observed with epoxides is the consequence of an isomerization process, whereas the result obtained with aziridines is explained by the absence of an effective substrate-nucleophile (amine) coordination. (C) 2009 Elsevier Ltd. All rights reserved.
• Stereospecific Uncatalyzed α-<i>O</i>-Glycosylation and α-<i>C</i>-Glycosidation by Means of a New <scp>d</scp>-Gulal-Derived α Vinyl Oxirane
  作者：Valeria Di Bussolo、Micaela Caselli、Maria Rosaria Romano、Mauro Pineschi、Paolo Crotti

  DOI：10.1021/jo0491152

  日期：2004.10.1

  The reaction of α vinyl oxirane 5, prepared through a new route to the d-gulal system, with O-nucleophiles (alcohols and di-O-isopropylidene-α-d-monosaccharides) and C-nucleophiles (lithium alkyls) affords, in a completely stereoselective way, the corresponding 2-unsaturated α O- and C-glycosides having the same configuration as the starting epoxide.

  通过新途径制得的通往d-古拉尔系统的α-乙烯基环氧乙烷5与O-亲核试剂（醇和二-O-异亚丙基-α - d-单糖）和C-亲核试剂（烷基锂）反应，得到一个完全立体选择性方式，相应的2-不饱和的α ø -和ç -glycosides具有相同的结构的起始环氧化物。