phenyl 2,3,4,6-tetra-O-benzyl-1-thio-D-mannopyranoside | 187226-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzyl-1-thio-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane
• CAS: 187226-51-3
• 化学式: C₄₀H₄₀O₅S
• 分子量: 632.821
• InChiKey: IKCMSYGNAFDJNX-QKMXTBNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzyl-1-thio-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 水 、 乙酸酐 、 二甲基亚砜 作用下， 以 丙酮 为溶剂， 生成 2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone
  参考文献：
  名称：

  Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction

  摘要：

  使用Zn粉和催化量的TMSCl作为活化剂，在Barbier反应条件下实现了糖1,5和1,4内酯的anomeric双二烯基化、单-β-罗汀基化和单-β-丙炔基化。合成的双二烯基衍生物经过环闭合烯烃复分解反应得到C-螺环戊烯糖苷。最后，将环戊烯环转化为基于碳水化合物的三环吗啉并三唑糖缀合物，作为潜在的SGLT2抑制剂。

  DOI：

  10.1039/c3ra46796a
• 作为产物：
  描述：

  苯硫酚 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction

  摘要：

  使用Zn粉和催化量的TMSCl作为活化剂，在Barbier反应条件下实现了糖1,5和1,4内酯的anomeric双二烯基化、单-β-罗汀基化和单-β-丙炔基化。合成的双二烯基衍生物经过环闭合烯烃复分解反应得到C-螺环戊烯糖苷。最后，将环戊烯环转化为基于碳水化合物的三环吗啉并三唑糖缀合物，作为潜在的SGLT2抑制剂。

  DOI：

  10.1039/c3ra46796a

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。
• Novel n-acetylglucosaminlytransferase and polynucleotide encoding the same
  申请人：——

  公开号：US20040132130A1

  公开（公告）日：2004-07-08

  The present invention relates to an enzyme having novel N-acetylglucosaminyltransferase (OMGnT) activity, a polynucleotide encoding the enzyme, a recombinant polynucleotide comprising the polynucleotide, a host cell comprising the recombinant polynucleotide, a method for producing an enzyme protein having OMGnT activity by culturing the host cell in a medium, and a method for modifying a sugar chain structure with the enzyme and a carbohydrate having a sugar chain structure modified by the method. This enzyme enables the production of complex carbohydrates, which could not be formed with conventional glycosyltransferases.

  本发明涉及一种具有新型N-乙酰葡糖胺基转移酶（OMGnT）活性的酶、一种编码该酶的多核苷酸、一种包含该多核苷酸的重组多核苷酸、一种包含该重组多核苷酸的宿主细胞、一种通过在培养基中培养宿主细胞来生产具有 OMGnT 活性的酶蛋白的方法，以及一种用该酶修饰糖链结构的方法和一种具有经该方法修饰的糖链结构的碳水化合物。这种酶可以生产复杂的碳水化合物，而传统的糖基转移酶无法形成这种复杂的碳水化合物。
• [EN] METHODS AND COMPOSITIONS FOR ENZYME-SPECIFIC ACTIVATION OF CARBOHYDRATE-CONJUGATED PRODRUGS<br/>[FR] METHODES ET COMPOSITIONS D'ACTIVATION SPECIFIQUE D'ENZYME DE PROMEDICAMENTS CONJUGUES A DES GLUCIDES
  申请人：UNIV OHIO STATE

  公开号：WO2006042056A3

  公开（公告）日：2006-10-26
• Stereospecific generation and analysis of α- and β-hemiacetals of monosaccharides in gas phase
  作者：Yuki Shioiri、Katsuhiko Suzuki、Shusaku Daikoku、Ayako Kurimoto、Yukishige Ito、Osamu Kanie

  DOI：10.1016/j.carres.2013.10.001

  日期：2013.12

  A series of Boc-protected 4-aminobutyl alpha- and beta-glycosides of commonly found neutral monosaccharides were synthesized. The sodium adducted ions of these individual molecules were used in producing corresponding alpha- and beta-anomers of hemiacetal species under collision-induced dissociation (CID) conditions. The Boc group was successfully removed under CID conditions producing 4-aminobutyl glycosides, which were then used as the precursors. An intramolecular attack of the aglyconic nitrogen atom onto C-1 position of aglycon assisted to leave hemiacetal ion species without affecting anomeric configurations. In this manner, stereospecific syntheses of sugar hemiacetals were first achieved in gas phase. The dissociation of sodium cation from a series of these hemiacetals was further studied according to energy-resolved mass spectrometry. In this study, it was found that all the sugar hemiacetals could be distinguished even if they have same m/z values. Furthermore, the order of affinity of Na+ toward the hemiacetals was determined. (C) 2013 Elsevier Ltd. All rights reserved.
• US7217548B2
  申请人：——

  公开号：US7217548B2

  公开（公告）日：2007-05-15