2-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-2-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxan-3-yl]isoindole-1,3-dione | 501089-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-2-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxan-3-yl]isoindole-1,3-dione
• CAS: 501089-71-0
• 化学式: C₃₅H₃₃NO₆S
• 分子量: 595.716
• InChiKey: NKEWPLUAZQLAFP-NRLOGRAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-2-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxan-3-yl]isoindole-1,3-dione 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到2,6-dideoxy-3,4-di-O-benzyl-2-N-phthalimido-6-S-(4-methylphenyl)-6-thio-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  DAST-Mediated Regioselective Anomeric Group Migration in Saccharides

  摘要：

  When saccharides bearing a sulfur, selenium, or oxygen substituent at the anomeric center and an unprotected hydroxyl group either at C-4 or C-6 were subjected to fluorination with DAST in dichloromethane, a regioselective migration of the anomeric substituent to the C-4 or C-6 position was observed. Certain saccharides gave a mixture of migration and normal fluorination products whereas others yielded mainly or exclusively migration products (beta-glycosyl fluorides). The high thermal and chemical stability of migrated glycosyl fluorides were demonstrated to be an important precursor for many significant carbohydrate analogies. It is therefore suggested that these migrations may have useful applications in organic synthesis.

  DOI：

  10.1021/jo900516r

文献信息

• β-Glycosylations with 2-Deoxy-2-(2,4-dinitrobenzenesulfonyl)-amino-glucosyl/galactosyl Selenoglycosides: Assembly of Partially <i>N</i>-Acetylated β-(1 → 6)-Oligoglucosaminosides
  作者：Dongwei Li、Jianjun Wang、Xianyang Wang、Zhi Qiao、Lingjun Wang、Peng Wang、Ni Song、Ming Li

  DOI：10.1021/acs.joc.3c00725

  日期：2023.7.7

  oligosaccharides. The power of this approach is highlighted by the efficient assembly of tri-, hexa-, and nonasaccharides composed of β-(1 → 6)-glucosaminosyl residues based on one-pot preparation of a triglucosaminosyl thioglycoside with DNs, phthaloyl, and 2,2,2-trichloroethoxycarbonyl as the protecting groups of amino groups. These glycans are potential antigens for developing glycoconjugate vaccines

  使用 PhSeCl/AgOTf 作为激活系统，建立了 2-脱氧-2-(2,4-二硝基苯磺酰基)氨基 (2dDNsNH)-吡喃葡萄糖基/吡喃半乳糖基硒糖苷的 β-糖基化的有效方案。该反应的特点是与多种空间位阻或亲核性较差的醇受体进行高度 β-选择性糖基化。硫代糖苷和硒代糖苷基醇被证明是可行的亲核试剂，为一锅法构建低聚糖开辟了新的机会。该方法的强大之处在于，基于具有 DN、邻苯二甲酰基和 2、 2,2-三氯乙氧基羰基作为氨基的保护基。这些聚糖是开发针对微生物感染的糖复合物疫苗的潜在抗原。
• Stereocontrolled Synthesis of <i>α</i>‐3‐Deoxy‐<scp>d</scp>‐manno‐oct‐2‐ulosonic Acid (<i>α</i>‐Kdo) Glycosides Using C3‐<i>p</i>‐Tolylthio‐Substituted Kdo Donors: Access to Highly Branched Kdo Oligosaccharides
  作者：Ao Sun、Zipeng Li、Yuchao Wang、Shuai Meng、Xiao Zhang、Xiangbao Meng、Shuchun Li、Zhongtang Li、Zhongjun Li

  DOI：10.1002/anie.202313985

  日期：2024.1.8

  glycosylation of 3-deoxy-d-manno-2-octulosonic acid (Kdo). The high reactivity and wide substrate scope of the donor enabled the synthesis of a range of Kdo-containing glycosides with complete α-stereoselectivity without the formation of 2,3-ene by-products. Several natural oligosaccharides were synthesized by a stepwise or one-pot process, including a highly branched Kdo pentasaccharide.

  已开发出一种用于 3-脱氧-d-甘露-2-辛糖酸 (Kdo) 糖基化的修饰供体。供体的高反应活性和广泛的底物范围使得能够合成一系列具有完全α-立体选择性的含Kdo糖苷，而不形成2,3-烯副产物。通过分步或一锅法合成了几种天然低聚糖，包括高度支化的 Kdo 五糖。