methyl (allyl 3,4-O-isopropylidene-β-D-galactopyranosid)uronate | 147221-64-5

• 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-O-isopropylidene-β-D-galactopyranosid)uronate
• CAS: 147221-64-5
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: YPFJUXLDHKJADB-APWOSFEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (allyl 3,4-O-isopropylidene-β-D-galactopyranosid)uronate 在 三氟甲磺酸 、 iodonium(di-γ-collidine) perchlorate 、 水 、 二正丁基氧化锡 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 正庚烷 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 40.67h， 生成 methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-galactopyranosyluronate)-(1->4)-(methyl 2,3-di-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：

  1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid, methyl ester 在 盐酸 、 乙酰溴 、 水 、 氰化汞 、 乙酸酐 、 对甲苯磺酸 、 mercury dibromide 作用下， 以 甲醇 、 氯仿 、 溶剂黄146 、 丙酮 为溶剂， 反应 51.0h， 生成 methyl (allyl 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

文献信息

• d-Galacturonic acid derivatives as acceptors and donorsin glycosylation reactions
  作者：Christian Vogel、Wolfram Steffan、Andrej Ya. Ott、Vitali I Betaneli

  DOI：10.1016/s0008-6215(92)84237-m

  日期：1992.12

  Jones oxidation of suitably protected allyl beta-D-galactopyranosides and subsequent esterification were reinvestigated. Partial deprotection of the resulting D-galacturonic acid derivatives afforded compounds suitable for transformation into glycosyl acceptors. The synthesis of 2-, 3-, and 4-trityl ethers, relying on efficient differential protecting-group strategies, is described. Trityl-cyanoethylidene

  重新研究了适当保护的烯丙基β-D-吡喃半乳糖苷的琼斯氧化反应和随后的酯化反应。所得D-半乳糖醛酸衍生物的部分脱保护得到适合转化为糖基受体的化合物。描述了依靠有效的差异保护基策略合成2-，3-和4-三苯甲基醚。这些三苯甲基醚的三苯甲基-氰基亚乙基缩合，导致被保护的二糖单元β-D-GalpA-（1-> 2）-D-GalpA和beta-D-GalpA-（1-> 3）-GalpA具有较高的证明了立体选择性。还制备了β-D-GalpA-（1→4）-D-GalpA二糖。