methyl 1-O-allyl-3,4-di-O-tert-butyldimethylsilyl-β-D-glucuronate | 616861-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1-O-allyl-3,4-di-O-tert-butyldimethylsilyl-β-D-glucuronate
• 英文别名: methyl (2S,3R,4R,5R,6R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-hydroxy-6-prop-2-enoxyoxane-2-carboxylate
• CAS: 616861-48-4
• 化学式: C₂₂H₄₄O₇Si₂
• 分子量: 476.758
• InChiKey: UXHQMQPWDXAKRB-PKRADWSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 、 methyl 1-O-allyl-3,4-di-O-tert-butyldimethylsilyl-β-D-glucuronate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以67%的产率得到methyl (2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-(allyl 3,4-di-O-tert-butyldimethylsilyl-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：

  (2S,3S,4R)-3,4-二乙酰氧基-3,4-二氢-2H-吡喃-2-羧酸甲酯 在 2-咪唑啉 、 dimethoxydioxirane*H₂O 、 sodium methylate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 122.0h， 生成 methyl 1-O-allyl-3,4-di-O-tert-butyldimethylsilyl-β-D-glucuronate
  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.