3,4,6-tri-O-benzyl-1,2-O-(allyloxyethylidene)-α-D-galactopyranose | 616861-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4,6-tri-O-benzyl-1,2-O-(allyloxyethylidene)-α-D-galactopyranose
• CAS: 616861-57-5
• 化学式: C₃₂H₃₆O₇
• 分子量: 532.634
• InChiKey: JMYCAGIYOGNKKF-LKWJADMRSA-N

物化性质

• 沸点：
  625.1±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-1,2-O-(allyloxyethylidene)-α-D-galactopyranose 在 Rh(PPh₃)Cl 三乙烯二胺 、 4-二甲氨基吡啶 、 氢氧化钾 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 65.0h， 生成 methyl (3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-(allyl 3,4-di-O-methoxymethyl-β-D-glucopyranosid)uronate
  参考文献：
  名称：

  Synthesis of the trisaccharide portion of soyasaponin βg: evaluation of a new glucuronic acid acceptor

  摘要：

  The synthesis of the trisaccharide portion of soyasaponin betag was successfully achieved using a new glucuronic acid acceptor: methyl 1-O-allyl-3 4-di-O-methoxymethyl-beta-D-glucuronate (9). This compound and methyl 1-O-allyl-3,4-di-O-tert-butyldimethyl-silyl-beta-D-glucuronate (8) were both prepared from glucuronolactone via a glycal intermediate. The former compound 9 was successfully coupled to ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-beta-D-galactopyranoside (13) in excellent yield. Synthesis of the protected trisaccharide was then completed by the addition of a suitably protected rhamnose derivative to the disaccharide portion. The reactivity of the glucuronic acid derivative 9 was also explored with trichloroacetimidate and fluoride donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00195-2
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 氢氧化钾 、 氢溴酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 24.5h， 生成 3,4,6-tri-O-benzyl-1,2-O-(allyloxyethylidene)-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of the trisaccharide portion of soyasaponin βg: evaluation of a new glucuronic acid acceptor

  摘要：

  The synthesis of the trisaccharide portion of soyasaponin betag was successfully achieved using a new glucuronic acid acceptor: methyl 1-O-allyl-3 4-di-O-methoxymethyl-beta-D-glucuronate (9). This compound and methyl 1-O-allyl-3,4-di-O-tert-butyldimethyl-silyl-beta-D-glucuronate (8) were both prepared from glucuronolactone via a glycal intermediate. The former compound 9 was successfully coupled to ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-beta-D-galactopyranoside (13) in excellent yield. Synthesis of the protected trisaccharide was then completed by the addition of a suitably protected rhamnose derivative to the disaccharide portion. The reactivity of the glucuronic acid derivative 9 was also explored with trichloroacetimidate and fluoride donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00195-2

文献信息

• Carboxymethylglycoside lactones (CMGLs): structural variations on the carbohydrate moiety
  作者：Arkadiusz Listkowski、Pisethnaline Ing、Rouba Cheaib、Stéphane Chambert、Alain Doutheau、Yves Queneau

  DOI：10.1016/j.tetasy.2007.09.007

  日期：2007.9

  New glucose and galactose based bicyclic lactones, with variations in the anomeric configuration, the protecting groups (acetyl or benzyl) and the furanosyl or pyranosyl rings were synthesized from allyl glycosides and used for the preparation of a series of new glycosylated alkyne amides.

  从烯丙基糖苷合成具有异头构型，保护基团（乙酰基或苄基）和呋喃糖基或吡喃糖基环的新的基于葡萄糖和半乳糖的双环内酯，并将其用于制备一系列新的糖基化炔烃酰胺。