allyl 2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside | 616861-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: allyl 2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enoxyoxan-3-yl] 4-nitrobenzoate
• CAS: 616861-63-3
• 化学式: C₃₇H₃₇NO₉
• 分子量: 639.702
• InChiKey: YTMYRWYWMUVJKY-YJOVGYIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside 在 Rh(PPh₃)Cl 三乙烯二胺 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 23.0h， 生成 2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate
  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：

  3,4,6-tri-O-benzyl-1,2-O-(allyloxyethylidene)-α-D-galactopyranose 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 allyl 2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside
  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

• Synthesis of the trisaccharide portion of soyasaponin βg: evaluation of a new glucuronic acid acceptor
  作者：Karen Plé

  DOI：10.1016/s0008-6215(03)00195-2

  日期：2003.7

  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.