benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate | 121409-22-1

• 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: benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate
• 英文别名: benzyl (2R,3R,4S)-3,4-diacetyloxy-2-[(1R,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 121409-22-1
• 化学式: C₂₆H₃₀O₁₃
• 分子量: 550.516
• InChiKey: HIRYSBFRDRCMAJ-KZQIJMTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 溴化钛(IV) 、 caesium carbonate 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 benzyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2,3-dideoxy-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  Nakamura, Mitsunobu; Furuhata, Kimio; Ogura, Haruo, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 12, p. 4807 - 4813

  摘要：

  DOI：

文献信息

• A Facile Access to Aryl <i>α</i>-Sialosides: the Combination of a Volatile Amine Base and Acetonitrile in Glycosidation of Sialosyl Chlorides
  作者：Atsuhito Kuboki、Takahiro Sekiguchi、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1055/s-1998-1717

  日期：1998.5

  We have succeeded in achieving a facile access to 4-nitrophenyl and 4-methylumbelliferyl-α-sialosides. To sialosyl chlorides which are fully protected with acetyl groups as glycosyl donors, the action of phenols with diisopropylethylamine in acetonitrile brought about high yield as well as facile product isolation.

  我们已经成功实现了对4-硝基苯基和4-甲基伞形酮-α-唾液酸苷的简易获取。对于完全被乙酰基保护的唾液酸氯化物作为糖基供体，在乙腈中使用二异丙基乙胺作用下的酚类物质带来了高产率以及简易的产品分离。
• A Novel Glycosylation of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) via in Situ Pyranose-Furanose Rearrangement.
  作者：Xue Long SUN、Toshitsugu KAI、Syuji FUJITA、Hiroaki TAKAYANAGI、Kimio FURUHATA

  DOI：10.1248/cpb.45.795

  日期：——

  In studies on the glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) derivatives, O-glycosides of furanose-type KDN were synthesized from benzyl 4, 5, 7, 8, 9-penta-O-acetyl-2-bromo-2, 3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate under Koenigs-Knorr reaction conditions. The furanoid structures of the KDN moiety were supported by with 1H-NMR experiments, and the reaction was considered as a novel glycosylation with ring contraction, which proceeded via in situ pyranose-furanose rearrangement of the KDN moiety, and subsequent coupling with acceptors.

  在对 3-脱氧-D-甘油-D-半乳糖-2-壬磺酸（KDN）衍生物的糖基化研究中，在柯尼希斯-克诺尔反应条件下，以 4, 5, 7, 8, 9-五-O-乙酰基-2-溴-2, 3-脱氧-D-甘油-D-半乳糖-2-壬磺吡喃糖酸苄酯为原料合成了呋喃糖型 KDN 的 O-糖苷。1H-NMR 实验证实了 KDN 分子的呋喃结构，并认为该反应是一种新型的缩环糖基化反应，是通过 KDN 分子的原位吡喃糖-呋喃糖重排以及随后与受体的偶联进行的。
• NAKAMURA, MITSUNOBU;FURUHATA, KIMIO;OGURA, HARUO, CHEM. AND PHARM. BULL., 36,(1988) N2, C. 4807-4813
  作者：NAKAMURA, MITSUNOBU、FURUHATA, KIMIO、OGURA, HARUO

  DOI：——

  日期：——