methyl (allyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosid)uronate | 311797-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (allyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosid)uronate
• CAS: 311797-06-5
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: NPFFUUBYMKFWBN-DIKXUDHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (allyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosid)uronate 在 水 、 silver trifluoromethanesulfonate 、 二正丁基氧化锡 、 silver carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 19.0h， 生成 methyl (methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Homogalacturonan Fragments

  摘要：

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.

  DOI：

  10.1080/07328300008544125
• 作为产物：
  描述：

  2-丙烯-1-基BETA-D-半乳吡喃糖醛酸甲酯2,3,4-三乙酸酯 在 盐酸 、 三氟甲磺酸 、 对甲苯磺酸 作用下， 以 甲醇 、 正庚烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 63.0h， 生成 methyl (allyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Homogalacturonan Fragments

  摘要：

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.

  DOI：

  10.1080/07328300008544125