4-O-benzoyl-3-O-benzyl-1,2-O-[1-(exo-cyano)ethylidene]-β-L-rhamnopyranose | 311350-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-benzoyl-3-O-benzyl-1,2-O-[1-(exo-cyano)ethylidene]-β-L-rhamnopyranose
• 英文别名: [(2S,3aR,5S,6S,7R,7aR)-2-cyano-2,5-dimethyl-7-phenylmethoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6-yl] benzoate
• CAS: 311350-22-8
• 化学式: C₂₃H₂₃NO₆
• 分子量: 409.439
• InChiKey: YQDNVGNEFGUKKN-VGNQLCOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-O-benzoyl-3-O-benzyl-1,2-O-[1-(exo-cyano)ethylidene]-β-L-rhamnopyranose 、 methyl (allyl 2,3-di-O-benzyl-4-O-trityl-β-D-galactopyranosid)uronate 在 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以47%的产率得到methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Rhamnogalacturonan I Fragments

  摘要：

  The partially deprotected trisaccharide 17 has been synthesized as an analogue of the repeating unit of the backbone of rhamnogalacturonan I. The trisaccharide 17 was obtained after prior selective derivatization of HO-3 and HO-4 of a rhamnopyranose cyanoethylidene glycosyl donor, followed by coupling with a tritylated galactopyranosyluronic acceptor (11), selective removal of the acetyl group at the O-2' position of the formed disaccharide 12, and glycosylation of the HO-2' position with methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-beta-D-galactopyranosid)uronate (14) providing methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-alpha-D-galactopyranosyluronate)-(1-->2)-(4-O-benzoyl-3-O-benzyl-alpha-L-rhamnopyranosyl)-(1-->4)-(allyl 2,3-di-O-benzyl-beta-D-galactopyranosid)uronate (15). Finally, palladium chloride catalyzed deallylation (16) and hydrogenolysis over Pd-C resulted in methyl (methyl alpha-D-galactopyranosyluronate)(1-->2)-(4-O-benzoyl-alpha-L-rhamnopyranosyl)-(1-->4)-alpha/beta D-galactopyranuronate (17).

  DOI：

  10.1080/07328300008544126
• 作为产物：
  描述：

  3,4-di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose 在 吡啶 、 盐酸 、 三氟甲磺酸 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 正庚烷 、 二氯甲烷 为溶剂， 反应 6.08h， 生成 4-O-benzoyl-3-O-benzyl-1,2-O-[1-(exo-cyano)ethylidene]-β-L-rhamnopyranose
  参考文献：
  名称：

  Synthesis of Rhamnogalacturonan I Fragments

  摘要：

  The partially deprotected trisaccharide 17 has been synthesized as an analogue of the repeating unit of the backbone of rhamnogalacturonan I. The trisaccharide 17 was obtained after prior selective derivatization of HO-3 and HO-4 of a rhamnopyranose cyanoethylidene glycosyl donor, followed by coupling with a tritylated galactopyranosyluronic acceptor (11), selective removal of the acetyl group at the O-2' position of the formed disaccharide 12, and glycosylation of the HO-2' position with methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-beta-D-galactopyranosid)uronate (14) providing methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-alpha-D-galactopyranosyluronate)-(1-->2)-(4-O-benzoyl-3-O-benzyl-alpha-L-rhamnopyranosyl)-(1-->4)-(allyl 2,3-di-O-benzyl-beta-D-galactopyranosid)uronate (15). Finally, palladium chloride catalyzed deallylation (16) and hydrogenolysis over Pd-C resulted in methyl (methyl alpha-D-galactopyranosyluronate)(1-->2)-(4-O-benzoyl-alpha-L-rhamnopyranosyl)-(1-->4)-alpha/beta D-galactopyranuronate (17).

  DOI：

  10.1080/07328300008544126

文献信息

• Synthesis of Rhamnogalacturonan I Fragments
  作者：Birte Nolting、Hanna Boye、Christian Vogel

  DOI：10.1080/07328300008544126

  日期：2000.1

  The partially deprotected trisaccharide 17 has been synthesized as an analogue of the repeating unit of the backbone of rhamnogalacturonan I. The trisaccharide 17 was obtained after prior selective derivatization of HO-3 and HO-4 of a rhamnopyranose cyanoethylidene glycosyl donor, followed by coupling with a tritylated galactopyranosyluronic acceptor (11), selective removal of the acetyl group at the O-2' position of the formed disaccharide 12, and glycosylation of the HO-2' position with methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-beta-D-galactopyranosid)uronate (14) providing methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-alpha-D-galactopyranosyluronate)-(1-->2)-(4-O-benzoyl-3-O-benzyl-alpha-L-rhamnopyranosyl)-(1-->4)-(allyl 2,3-di-O-benzyl-beta-D-galactopyranosid)uronate (15). Finally, palladium chloride catalyzed deallylation (16) and hydrogenolysis over Pd-C resulted in methyl (methyl alpha-D-galactopyranosyluronate)(1-->2)-(4-O-benzoyl-alpha-L-rhamnopyranosyl)-(1-->4)-alpha/beta D-galactopyranuronate (17).