1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose | 20113-43-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose
• 英文别名: 1,2,3,4-Tetra-O-acetyl-6-O-tosyl-α-D-glucopyranose；O¹,O²,O³,O⁴-tetraacetyl-O⁶-(toluene-4-sulfonyl)-α-D-glucopyranose；O¹,O²,O³,O⁴-Tetraacetyl-O⁶-(toluol-4-sulfonyl)-α-D-glucopyranose；Tetra-O-acetyl-O⁶-toluol-4-sulfonyl-α-D-glucopyranose；6-O-Tosyl-1,2,3,4-tetra-O-acetyl-α-D-glucopyranose；[(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-2-[(4-methylphenyl)sulfonyloxymethyl]oxan-3-yl] acetate
• CAS: 20113-43-3
• 化学式: C₂₁H₂₆O₁₂S
• 分子量: 502.496
• InChiKey: IWKNNNHECVVJTH-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  157.8
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose 在 乙酸酐 、 sodium iodide 作用下， 生成 acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside
  参考文献：
  名称：

  关于由葡萄糖生产α-和β-异戊糖四乙酸酯

  摘要：

  DOI：

  10.1002/hlca.19460290530
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranose 在 高氯酸 、 乙酸酐 作用下， 生成 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose
  参考文献：
  名称：

  Roberts et al., 1968, vol. 7, p. 311,317

  摘要：

  DOI：

文献信息

• 1,6-Anhydro-1-thio-β-D-glucopyranose (Thiolevoglucosan) and the Corresponding Sulfoxides and Sulfone
  作者：Miloš Buděšínský、Jana Poláková、Michaela Hamerníková、Ivana Císařová、Tomáš Trnka、Miloslav Černý

  DOI：10.1135/cccc20060311

  日期：——

  Starting 1,2,3,4-tetra-O-acetyl-6-O-tosyl-β-D-glucopyranose (3) was converted into 2,3,4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose (6) via intermediate glycosyl bromide 4 and S-thiouronium salt 5. Treatment of compound 6 with sodium methoxide gave 1,6-anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan 2a). The isomeric sulfoxides 7 and 8 were prepared by selective oxidation of thiolevoglucosan 2a with hydrogen peroxide or 3-chloroperoxybenzoic acid. The structure of new compounds was confirmed by ¹H and ¹³C NMR spectroscopy or by X-ray analysis; magnetic anisotropy of the sulfinyl and sulfonyl group has been discussed.

  将1,2,3,4-四O-乙酰基-6-O-对甲苯磺酰基-β-D-葡萄糖吡喃糖（3）转化为2,3,4-三O-乙酰基-1-硫-6-O-对甲苯磺酰基-β-D-葡萄糖吡喃糖（6），通过中间体糖溴化物4和S-硫代脲盐5。用甲氧基钠处理化合物6得到1,6-脱水-1-硫-β-D-葡萄糖吡喃糖（硫代乙基葡萄糖2a）。异构的亚砜7和8通过过氧化氢或3-氯过氧苯甲酸选择性氧化硫代乙基葡萄糖2a制备。新化合物的结构通过¹H和¹³C核磁共振或X射线分析确认；讨论了亚砜基和磺酰基的磁各向异性。
• Synthesis of sulfur-linked analogues of nigerose, laminarabiose, laminaratriose, gentiobiose, gentiotriose, and laminaran trisaccharide Y
  作者：Marie-Odile Contour-Galcera、Jean-Michel Guillot、Carmen Ortiz-Mellet、Françoise Pflieger-Carrara、Jacques Defaye、Jacques Gelas

  DOI：10.1016/0008-6215(95)00339-8

  日期：1996.2

  Sulfur-linked analogues of 3-O-alpha-D-glucopyranosyl-D-glucose (nigerose), 3-O-beta-D-glucopyranosyl-D-glucose (laminarabiose), 6-O-beta-D-glucopyranosyl-D-glucose (gentiobiose), O-beta-D-glucopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->3)-D-glucos e (laminaratriose), O-beta-D-glucopyranosyl)-(1-->6)-O-beta-D-glucopyranosyl-(1-->6)-D-gluco se (gentiotriose) and 3,6-di-O-beta-D-glucopyranosyl-D-glucose

  N-二甲基甲酰胺（用于6和21）或在四氢呋喃中在冠醚存在下（用于11）。涉及非异构硫醇盐与2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基溴化物反应的序列可替代地用于制备11和21，但事实证明不太令人满意。硫代三糖16、29和37的制备涉及混合方法。
• Phosphatidylinositol 3-Phosphate Mimics Based on a Sulfoquinovose Scaffold: Synthesis and Evaluation as Protein Kinase B Inhibitors
  作者：Luca Gabrielli、Ilaria Calloni、Giulia Donvito、Barbara Costa、Noemi Arrighetti、Paola Perego、Diego Colombo、Fiamma Ronchetti、Francesco Nicotra、Laura Cipolla

  DOI：10.1002/ejoc.201402664

  日期：2014.9

  New sulfoquinovose analogues of phosphatidylinositol 3-phosphate have been synthesised based on a sulfoquinovose scaffold as potential protein kinase B (PKB) inhibitors. The synthetic strategy involved the introduction into glucose of a thioacetate group at the 6-position and of an azide group at the anomeric position as precursors of the sulfonate and phosphoramidate moieties present in the final

  基于磺基奎诺糖支架合成了新的 3-磷酸磷脂酰肌醇磺基奎诺糖类似物，作为潜在的蛋白激酶 B (PKB) 抑制剂。合成策略包括将 6 位硫代乙酸酯基团和异头位置的叠氮基团引入葡萄糖，作为最终化合物中存在的磺酸盐和氨基磷酸酯部分的前体。合成的化合物通过 ELISA 测定在体外对分离的 PKB 进行了测试，并测试了它们对人卵巢癌细胞系 IGROV-1 的抗增殖活性。磺基喹诺酮衍生物 2b 和 2c 在低微摩尔范围内显示出抑制活性。
• The Synthesis of Various 1,6-Disulfide-Bridged D-Hexopyranoses
  作者：Ethan D. Goddard-Borger、Robert V. Stick

  DOI：10.1071/ch04277

  日期：——

  1,6-Disulfide-bridged derivatives have been prepared for d-gluco-, d-manno-, d-allo-, d-galacto-, and d-talo-pyranose, in the main by the nucleophilic attack of a C6 thiolate onto an anomeric thiosulfonate. The d-gluco disulfide, ‘angyalosan’, was successfully oxidized to a single thiosulfinate.

  1,6 二甲基二硫键衍生物的制备主要是通过 C6 硫代硫酸酯与异构体硫代磺酸酯的亲核反应，制备出了 d-葡糖、d-甘露糖、d-异甘露糖、d-半乳糖和 d-塔罗吡喃糖。d- 葡萄糖二硫化物 "anggyalosan "被成功氧化成单一的硫代亚硫酸盐。
• Ohle; v. Vargha, Chemische Berichte, 1929, vol. 62, p. 2425,2433
  作者：Ohle、v. Vargha

  DOI：——

  日期：——