methyl 1,5-anhydro-2-deoxy-3,4-di-O-methoxymethyl-D-arabino-hex-1-enuronate | 616861-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 1,5-anhydro-2-deoxy-3,4-di-O-methoxymethyl-D-arabino-hex-1-enuronate
• 英文别名: methyl (2S,3S,4R)-3,4-bis(methoxymethoxy)-3,4-dihydro-2H-pyran-2-carboxylate
• CAS: 616861-47-3
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: PGRHVUVVUXREEN-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 1,5-anhydro-2-deoxy-3,4-di-O-methoxymethyl-D-arabino-hex-1-enuronate 在 氢氧化钾 、 三氟甲磺酸三甲基硅酯 、 dimethoxydioxirane*H₂O 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 158.0h， 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：

  (2S,3S,4R)-3,4-二乙酰氧基-3,4-二氢-2H-吡喃-2-羧酸甲酯 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 methyl 1,5-anhydro-2-deoxy-3,4-di-O-methoxymethyl-D-arabino-hex-1-enuronate
  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.