ethyl 2,3,4-tri-O-benzoyl-1-thio-α-D-glucopyranoside | 473545-24-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,4-tri-O-benzoyl-1-thio-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-6-ethylsulfanyl-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 473545-24-3
• 化学式: C₂₉H₂₈O₈S
• 分子量: 536.603
• InChiKey: PYWMPKYQOUDVQQ-VYZOEPQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4-tri-O-benzoyl-1-thio-α-D-glucopyranoside 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86%的产率得到ethyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-1-thio-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  (2R,3S,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 ethyl 2,3,4-tri-O-benzoyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  一锅顺序立体选择性糖基化聚合合成寡糖

  摘要：

  F1α 抗原是肿瘤相关 O 联粘蛋白糖基氨基酸的一个成员，通过一锅序贯糖基化进行了会聚全合成。通过结合三氟甲磺酸三苯甲基酯 (TrOTf) 和 N-碘代琥珀酰亚胺 (NIS) 成功地进行了氨基酸 7 与硫糖苷 6 的高度 α 选择性糖基化，以高产率 (97%, α/β = 83⁄17) 得到糖基氨基酸 21 ）。接下来，通过三苯甲基四(五氟苯基)硼酸酯[TrB(C6F5)4]或三氟甲磺酸(TfOH)的促进，尝试了硫代糖苷4与半乳糖苯基碳酸酯2或氟化物3的糖基化；通过进一步添加糖基氨基酸 5 和 NIS，分别以 80% 或 89% 的总产率提供受保护的 F1α 25。去除保护基团后以高产率获得所需的三糖。下一个，

  DOI：

  10.1246/bcsj.76.1829

文献信息

• Phenylselenoglycosides as novel, versatile glycosyl donors. Selective activation over thioglycosides
  作者：Seema Mehta、B. Mario Pinto

  DOI：10.1016/0040-4039(91)80005-q

  日期：1991.1

  of phenylselonoglycosides over ethylthioglycosides with silver trifluoromethanesulfonate and anhydrous potassium carbonate gives an efficient synthesis of disaccharides from selenoglycoside donors and thioglycoside acceptors. Activation is quenched by addition of 1,1,3,3,-tetramethylurea or collidine.

  用三氟甲磺酸银和无水碳酸钾对乙基巯基糖苷在乙基硫代糖苷上的选择性活化，可以从硒代糖苷供体和硫代糖苷受体高效合成二糖。通过添加1,1,3,3，-四甲基脲或可力丁淬灭活化。
• Convergent and Convenient Total Synthesis of Phytoalexin-Elicitor Active Heptasaccharide by One-Pot Sequential Glycosylation
  作者：Teruaki Mukaiyama、Kazuhiro Ikegai、Takashi Hashihayata、Koichi Kiyota、Hideki Jona

  DOI：10.1246/cl.2002.730

  日期：2002.7

  Convergent and convenient total synthesis of branched hepta-β-glucoside 1 having phytoalexin-elicitor activity was efficiently accomplished by way of two one-pot sequential glycosylation reactions. Trisaccharide 8 was synthesized in high yield by TfOH-catalyzed one-pot glycosylation using three component monosaccharides and subsequent selective deprotection of a 6′-O-TBDPS group. The second one-pot

  通过两个一锅连续糖基化反应有效地完成了具有植物抗毒素激发剂活性的支链七-β-葡萄糖苷 1 的收敛和方便的全合成。通过使用三组分单糖和随后的 6'-O-TBDPS 基团的选择性脱保护，通过 TfOH 催化的一锅糖基化以高产率合成了三糖 8。三糖8与三个单糖的第二次一锅糖基化顺利进行，立体选择性地得到七葡糖苷11，基于单糖3的总收率为48%。去除保护基团后，目标化合物1以高收率获得。
• DAST-Mediated Regioselective Anomeric Group Migration in Saccharides
  作者：Po-Chiao Lin、Avijit Kumar Adak、Shau-Hua Ueng、Li-De Huang、Kuo-Ting Huang、Ja-an Annie Ho、Chun-Cheng Lin

  DOI：10.1021/jo900516r

  日期：2009.6.5

  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.
• Convergent Total Syntheses of Oligosaccharides by One-Pot Sequential Stereoselective Glycosylations
  作者：Takashi Hashihayata、Kazuhiro Ikegai、Kazuya Takeuchi、Hideki Jona、Teruaki Mukaiyama

  DOI：10.1246/bcsj.76.1829

  日期：2003.9

  amino acid 7 with thioglycoside 6 was successfully carried out by combining trityl trifluoromethanesulfonate (TrOTf) and N-iodosuccimide (NIS) which gave glycosyl amino acid 21 in high yield (97%, α/β = 83⁄17). Next, the glycosylation of thioglycoside 4 with galactosyl phenyl carbonate 2 or fluoride 3 was tried by the promotion of trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4] or trifluoromethanesulfonic

  F1α 抗原是肿瘤相关 O 联粘蛋白糖基氨基酸的一个成员，通过一锅序贯糖基化进行了会聚全合成。通过结合三氟甲磺酸三苯甲基酯 (TrOTf) 和 N-碘代琥珀酰亚胺 (NIS) 成功地进行了氨基酸 7 与硫糖苷 6 的高度 α 选择性糖基化，以高产率 (97%, α/β = 83⁄17) 得到糖基氨基酸 21 ）。接下来，通过三苯甲基四(五氟苯基)硼酸酯[TrB(C6F5)4]或三氟甲磺酸(TfOH)的促进，尝试了硫代糖苷4与半乳糖苯基碳酸酯2或氟化物3的糖基化；通过进一步添加糖基氨基酸 5 和 NIS，分别以 80% 或 89% 的总产率提供受保护的 F1α 25。去除保护基团后以高产率获得所需的三糖。下一个，