methyl (allyl 3,4-di-O-acetyl-β-D-galactopyranosid)uronate | 311797-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (allyl 3,4-di-O-acetyl-β-D-galactopyranosid)uronate
• CAS: 311797-11-2
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: UCKZZYLUHWKHMM-MPLKPFFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (allyl 3,4-di-O-acetyl-β-D-galactopyranosid)uronate 在 三氟甲磺酸 、 水 、 sodium acetate 、 palladium dichloride 作用下， 以 正庚烷 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-galactopyranosiduronate
  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 disodium hydrogenphosphate 、 potassium dihydrogenphosphate 、 Acylase I 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以95%的产率得到methyl (allyl 3,4-di-O-acetyl-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