2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol | 4132-32-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol
• 英文别名: (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-methane α anomer；(2R,3S,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 4132-32-5
• 化学式: C₃₅H₃₈O₅
• 分子量: 538.684
• InChiKey: WIWPUDCFWHDUNF-KFTXORTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-methyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  碳水化合物化学中的巯基化：α-D- C-葡萄糖吡喃糖基衍生物的高度立体选择性路线

  摘要：

  使用Witting反应将由碳水化合物2,3,4,6-四-O-苄基-D-吡喃葡萄糖制备的烯烃进行商品化，提供了轴向氯汞醚作为唯一的分离产物，从而提供了第一个立体定向途径1,5-反式-（例如α - D）C-吡喃葡萄糖基衍生物。

  DOI：

  10.1039/c39810000375
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 偶氮二异丁腈 、 tributyl hydride 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol
  参考文献：
  名称：

  硒在碳水化合物化学中的用途：C-糖苷同源物的制备

  摘要：

  摘要将3,4,5,7-四-O-苄基-d-葡萄糖-庚-1-烯醇进行硒环化-氧化消除序列，以提供2,6-脱水-3,4,5,7-四-O-苄基-1-脱氧-d-葡萄糖-庚-1-烯醇，产率为54％。用N-苯基硒代邻苯二甲酰亚胺处理甲基2,3,4-三-O-苄基-α-d-吡喃葡萄糖苷，得到甲基2,3,4-三-O-苄基-6-脱氧-6-苯基硒代-α-d-吡喃葡萄糖苷，其被转化为甲基2,3,4-三-O-苄基-6-脱氧-α-d-木糖-己基-5-烯吡喃糖苷。

  DOI：

  10.1016/0008-6215(85)85210-1

文献信息

• Organometallics in organic synthesis. Applications of a new diorganozinc reaction to the synthesis of C-glycosyl compounds with evidence for an oxonium-ion mechanism
  作者：Alan P. Kozikowski、Toshiro Konoke、Allen Ritter

  DOI：10.1016/s0008-6215(00)90882-6

  日期：1987.12

  features of a new organozinc-based substitution process [heteroatom-C-(R1,R2)-SPh + R3(2)Zn----heteroatom-C-(R1,R2,R3)], first discovered during a total synthesis of the alkaloid mycotoxin alpha-cyclopiazonic acid, are described. Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process. Since these sulfur compounds are converted into C-glycosyl compounds with some

  首次发现新的基于有机锌的取代过程[杂原子-C-（R1，R2）-SPh + R3（2）Zn ----杂原子-C-（R1，R2，R3）]的机理和立体化学特征在生物碱真菌毒素的全合成过程中，描述了α-环吡嗪酸。苯基硫代糖苷是研究该反应过程性质的有价值的底物。由于这些硫化合物以一定的立体选择性转化为C-糖基化合物，因此有机锌化学确实为这些生物活性物质提供了新的进入途径。
• Reactions of glycosyl fluorides. Synthesis of C-glycosides
  作者：K. C. Nicolaou、Roland E. Dolle、Alexander Chucholowski、Jared L. Randall

  DOI：10.1039/c39840001153

  日期：——

  Glycosyl fluorides were found to react with a number of nucleophilic reagents with or without catalysis leading to a variety of C-glycosides and related compounds.

  发现糖基氟化物在催化作用或不催化作用下与许多亲核试剂反应，从而导致多种C-糖苷和相关化合物。
• Mannose derivatives for treating bacterial infections
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US10669298B2

  公开（公告）日：2020-06-02

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula I: The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

  本发明涉及可用于治疗或预防细菌感染的化合物。这些化合物具有式 I： 本发明还提供了含有这些化合物的药学上可接受的组合物，以及使用这些组合物治疗细菌感染的方法。最后，本发明提供了制造本发明化合物的工艺。
• Glycosylidene Carbenes, Part 29 , Insertion into B−C and Al−C Bonds: Glycosylborinates, -boranes, and -alanes
  作者：Wolfgang Wenger、Andrea Vasella

  DOI：10.1002/1522-2675(20000705)83:7<1542::aid-hlca1542>3.0.co;2-f

  日期：2000.7.5

  Insertion of the glycosylidene carbenes derived from the diazirines 1, 14 and 15 into the B-alkyl bond of the B-alkyl-9-oxa-10-borabicyclo[3.3.2]decanes 5, 6, and 7 yielded the stable glycosylborinates 8/9 (55%, 55:45), 10/11 (31%, 65:35), 12/13 (47%, 60:40), 16/17 (55%, 55:45), 18/19 (47%, 45:55), and 20/21 (31%, 30:70). Crystal-structure analysis of 17 and NOEs of 9 and 19 show that 17 9, and 19 adopt similar conformations. The glycosylborinates are stable under acidic, basic and thermal conditions. The unprotected glycosylborinate 25 was obtained in 80% by hydrogenolysis of 12. Insertion of the glycosylidene carbene derived from the diazirine 1 into a B-C bond of BEt3, BBu3, and BPh3 led to unstable glycosylboranes that were oxidised to yield the hemiacetals 29 (55%), 31 (45%), and 33 (48%), respectively, besides the glucals 30 (13%), 32 (20%), and 34 (20%), respectively. Insertion of the glycosylidene carbenes derived from 14 and 15 into a B - C bond of BEt3 led exclusively to hemiacetals; only 15 yielding traces of the glucal 40 besides the hemiacetal 39. The glycosylidene carbene derived from 1 reacted with AL(Bu-1), and AlMe3 to generate reactive glycosylalanes that were hydrolysed, yielding the C-glycosides 46 (21%) and 49 (30%), respectively besides the glucals 48 (26%) and 51 (30%); deuteriolysis instead of protonolysis led to the monodeuterio analogues of 46 and 49, respectively, which possess an equatorial H-2-atom at the anomeric center.
• BIHOVSKY, RON;SELICK, CARYN;GIUSTI, IRENA, J. ORG. CHEM., 53,(1988) N 7, C. 4026-4031
  作者：BIHOVSKY, RON、SELICK, CARYN、GIUSTI, IRENA

  DOI：——

  日期：——