3-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose | 82740-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose
• 英文别名: 3-O-acetyl-1,2-O-[1-(exo-cyano)ethylidene]-β-L-rhamnopyranose
• CAS: 82740-02-1
• 化学式: C₁₁H₁₅NO₆
• 分子量: 257.243
• InChiKey: RJGVRJLBYFIKPW-MVPQHZIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  98.01
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose 在 吡啶 、 盐酸 、 三氟甲磺酸 作用下， 以 甲醇 、 正庚烷 、 二氯甲烷 为溶剂， 反应 50.0h， 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
• 作为产物：
  描述：

  乙酰氯 、 1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose 在 吡啶 作用下， 以 甲苯 为溶剂， 生成 3-O-acetyl-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 a heteroglycuronan derivative containingthe β-
  作者：Christian Vogel、Wolfram Steffan、Hanna Boye、Helmut Kristen、Vitali I Betaneli、Andrej Ya. Ott、Nikolay K Kochetkov

  DOI：10.1016/s0008-6215(92)84238-n

  日期：1992.12

  Helferich glycosylation of the cyanoethylidene L-rhamnose derivative 3 with the galactosyluronic bromide 2 gave the disaccharide 4 as a key intermediate in the synthesis of the monomer 13 for trityl-cyanoethylidene condensation (TCC). The following formation of the monomer 13, including introduction of a trityl group at O-3', proceeded in six steps. Because of the difficulty of some steps, an alternative route for 13 was tested. Model compounds 20, 21, and 22 were synthesized in order to confirm the stereoregularity of the products of the polycondensation. The polycondensation of the monomer gave D-GalpA-(1 --> 3)-L-Rha-oligomer derivatives consisting mainly of three repeating units. This result is in contrast with the degree of polymerisation (dp greater-than-or-equal-to 22) of other synthetic rhamnans, but is very similar to dp 2-7 of homo- and hetero-glucuronan derivatives.