2,3,6,2',3',4',6'-hepta-O-acetyl-2S-acetyl cellobioside | 205451-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6,2',3',4',6'-hepta-O-acetyl-2S-acetyl cellobioside
• 英文别名: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-S-acetyl-β-D-glucopyranose；2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-S-acetyl-1-thio-β-D-glucopyranose；2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1→4)-2,3,6-tri-O-acetyl-l-S-acetyl-1-thio-β-D-glucopyranose；acetyl 2,3,6-tri-O-acetyl-4-O-[2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl]-1-thio-β-D-glucopyranoside；O²,O³,O⁶,S-Tetraacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranose
• CAS: 205451-24-7
• 化学式: C₂₈H₃₈O₁₈S
• 分子量: 694.665
• InChiKey: FRXVJYSARLMCLR-AXXYRMHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  228.86
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-2S-acetyl cellobioside 在 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl α-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl-(1->4)-β-(2,3,6-tri-O-acetyl-D-glucopyranosyl)-(1->4)-β-2,3,6-tri-O-benzoyl)-4-thio-D-glucoside
  参考文献：
  名称：

  纤维三糖和纤维四糖类似物的合成，作为纤维素酶机理研究的过渡态模拟物

  摘要：

  带有环己烯环的纤维三糖和纤维四糖类似物被开发为分子探针，有望模拟纤维素酶水解的过渡态构象。将环己烯环置于吡喃糖环上，预期其位于酶的-1个亚位点。为了评估这些探针，还合成了纤维三糖和纤维四糖的硫衍生物作为模拟天然纤维素稳定构象的耐酶类似物。使用差示扫描量热法的结合测定法表明，引入环己烯环对于与来自腐质霉（Humicola insolens）的内切葡聚糖酶NCE5的络合是有效的。

  DOI：

  10.1016/j.bmc.2011.04.048
• 作为产物：
  描述：

  乙酰溴代纤维二糖 在 乙醇 、 sodium acetate 、 锌 作用下， 生成 2,3,6,2',3',4',6'-hepta-O-acetyl-2S-acetyl cellobioside
  参考文献：
  名称：

  Wrede; Hettche, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1927, vol. 172, p. 169,173

  摘要：

  DOI：

文献信息

• Improved Synthesis of 1‐Glycosyl Thioacetates and Its Application in the Synthesis of Thioglucoside Gliflozin Analogues
  作者：Guang‐Jing Feng、Shuang‐Shuang Wang、Jian Lv、Tao Luo、Yuzhou Wu、Hai Dong

  DOI：10.1002/ejoc.202100357

  日期：2021.6.7

  We reported relative green synthesis of 1-thioglycosides by straightforward reaction of per-O-acetylated glycoses with KSAc in EtOAc. Furthermore, the highly efficient method to synthesize per-O-acetylated glycosyl disulfide and glycosyl 1-thiol were developed. Based on this, the synthesis of auranofin was improved and two thioglucoside gliflozin analogues (possible SGLT inhibitors) were efficiently

  我们报道的1-硫代糖苷相对绿色合成由per-的直接的反应Ó于EtOAc -acetylated葡糖与KSAc。此外，还开发了合成过氧乙酰化糖基二硫化物和糖基 1-硫醇的高效方法。在此基础上，金诺芬的合成得到改进，并以高产率高效合成了两种硫代葡萄糖苷格列净类似物（可能是 SGLT 抑制剂）。
• Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy
  作者：Ya-Nan Ding、Yan-Chong Huang、Wei-Yu Shi、Nian Zheng、Cui-Tian Wang、Xi Chen、Yang An、Zhe Zhang、Yong-Min Liang

  DOI：10.1021/acs.orglett.1c01723

  日期：2021.8.6

  We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%,

  我们描述了一种用于制备（杂）芳基硫代/硒糖苷的新型钯催化多米诺骨牌程序。容易获得的（杂）芳基碘化物和容易获得的 1-硫糖/1-硒糖被用作底物。同时，10种糖类与该反应相容，具有良好的区域选择性和立体选择性、高效率和广泛的适用性（高达89%，53例）。该方法能够直接形成（杂）芳基硫代/硒糖苷的 C(sp 2 )–S/Se 键。
• Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues
  作者：Penghua Shu、Jing Zeng、Jinyi Tao、Yueqi Zhao、Guangmin Yao、Qian Wan

  DOI：10.1039/c5gc00084j

  日期：——

  Highly efficient selective S-deacetylations were achieved by simple transthioesterification under mild basic conditions.

  通过在温和的碱性条件下进行简单的硫代酯基转移，即可实现高效的选择性S-脱乙酰基作用。
• Chemoenzymatic Synthesis of a Bifunctionalized Cellohexaoside as a Specific Substrate for the Sensitive Assay of Cellulase by Fluorescence Quenching
  作者：Viviane Boyer、Sébastien Fort、Torben P. Frandsen、Martin Schülein、Sylvain Cottaz、Hugues Driguez

  DOI：10.1002/1521-3765(20020315)8:6<1389::aid-chem1389>3.0.co;2-#

  日期：2002.3.15

  A new bifunctionalized cellohexaose derivative was synthesized as a specific substrate for continuous assay of cellulases by resonance energy transfer. This cellohexaoside has a naphthalene moiety (EDANS) as a fluorescent energy donor at the reducing end and a 4-(4'-dimethylaminobenzeneazo)-benzene derivative as an acceptor chromophore at the non-reducing end. The key steps for the preparation of the

  合成了一种新的双功能纤维六糖衍生物作为特定底物，用于通过共振能量转移连续测定纤维素酶。该纤维六糖苷在还原端具有萘部分（EDANS）作为荧光能量供体，在非还原端具有4-（4'-二甲基氨基苯偶氮）-苯衍生物作为受体生色团。制备靶分子的关键步骤涉及纤维二糖基和纤维四糖基氟化物供体的糖基化反应到腐殖质纤维素酶Cel7B的E197A突变体催化的纤维二糖基受体上。用各种纤维素酶消化后，能量转移被破坏，并且观察到荧光增加。
• Family of thiomercuric derivatives of sugars: Synthesis, fungicidal/herbicidal activity, and application to the X‐ray structure determination of the corresponding enzymes
  作者：Valery Belakhov、Evgenia Dor、Joseph Hershenhorn、Mark Botoshansky、Tsafrir Bravman、Mirit Kolog、Yuval Shoham、Gil Shoham、Timor Baasov

  DOI：10.1560/e8dm-02pk-dl0v-u7fr

  日期：2000.12

  A series of thiomercuric derivatives of mono‐ and disaccharides 1–7, in which methylmercury or phenylmercury is covalently attached to anomeric thioglycosides, were synthesized for structure—function studies of glycosidases. Thiomethylmercuryl xylobiosides 5 and 6 were found to inhibit intracellular xylanase‐T6 in a competitive manner, with K_i values of 0.35 mM and 0.01 mM, respectively. These inhibitors have been co‐crystallized with the enzyme and are being used for X‐ray analysis. 1‐(Thiomethylmercuric)‐ß‐D‐xyloside (3) affords crystals belonging to the orthorhombic space group P2₁2₁2₁ and at 293(2) K: a = 6.7510(2), b = 9.7140(2), c = 29.4770(9) Å, V = 1933.08(9) Å, Z = 8, R(F²) = 0.0329, and R_w(F²) = 0.0626. There are two molecules (A and B) in the asymmetric unit, and each one shows an almost linear S–Hg–C arrangement. Biological tests on 1–7 indicated that they exhibit potent fungicidal and herbicidal activities.

  摘要 合成了一系列单糖和二糖的硫代汞衍生物1-7，其中甲基汞或苯基汞共价连接到硫代糖苷的异构体上，用于糖苷酶的结构-功能研究。研究发现，硫代甲基汞木糖苷 5 和 6 能以竞争方式抑制细胞内的木聚糖酶-T6，其 Ki 值分别为 0.35 mM 和 0.01 mM。这些抑制剂已与该酶共同结晶，目前正用于 X 射线分析。1-(Thiomethylmercuric)-ß-D-xyloside (3) 结晶属于正交空间群 P212121，在 293(2) K 时：a = 6.7510(2)，b = 9.7140(2)，c = 29.4770(9)埃，V = 1933.08(9)埃，Z = 8，R(F2) = 0.0329，Rw(F2) = 0.0626。不对称单元中有两个分子（A 和 B），每个分子几乎都呈线性 S-Hg-C 排列。对 1-7 进行的生物测试表明，它们具有很强的杀真菌和除草活性。