| 46398-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 46398-94-1
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: LONPUHGGLPYIAW-OKNNCHMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.01
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of β-(1→6)-branched β-(1→3) glucohexaose and its analogues containing an α-(1→3) linked bond with antitumor activity

  摘要：

  A beta-(1 --> 6)-branched beta-(1 --> 3)-glucohexaose, present in many biologically active polysaccharides from traditionally herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, was synthesized as its lauryl glycoside 32, and its analogues 18, 20 and 33 containing an alpha-(l --> 3) linked bond were synthesized. It is interesting to find that coupling of a 3,6-branched acylated trisaccharide trichloroacetimidate donor 9 with 3,6-branched acceptors 13 and 16 with 3'-OH gave the alpha-(1 --> 3)linked hexasaccharides 17 and 19, respectively, in spite of the presence of C-2 ester capable of neighboring group participation. However, coupling of 9 with 4-methoxyphenyl 4,6-0-benzylidene-beta-D-glucopyranoside (27) selectively gave beta-(1 --> 3)-linked tetrasaccharide 28. Simple chemical transformation of the tetrasaccharide 28 gave acylated tetrasaccharide trichloroacetimidate 29. Coupling of 29 with lauryl (I --> 6)-linked disaccharide 26 with 3-OH gave beta-(I --> 3)-linked hexasaccharide 30 as the major product. Bioassay showed that in combination with the chemotherapeutic agent cyclophospamide (CPA), the hexaose 18 at a dose of 0.5-1 mg/kg substantially increased the inhibition of S 180 for CPA, but decreased the toxicity caused by CPA. Some of these oligosaccharides also inhibited U-14 noumenal tumor in mice effectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00118-4
• 作为产物：
  描述：

  D-葡萄糖 在 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis of β-(1→6)-branched β-(1→3) glucohexaose and its analogues containing an α-(1→3) linked bond with antitumor activity

  摘要：

  A beta-(1 --> 6)-branched beta-(1 --> 3)-glucohexaose, present in many biologically active polysaccharides from traditionally herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, was synthesized as its lauryl glycoside 32, and its analogues 18, 20 and 33 containing an alpha-(l --> 3) linked bond were synthesized. It is interesting to find that coupling of a 3,6-branched acylated trisaccharide trichloroacetimidate donor 9 with 3,6-branched acceptors 13 and 16 with 3'-OH gave the alpha-(1 --> 3)linked hexasaccharides 17 and 19, respectively, in spite of the presence of C-2 ester capable of neighboring group participation. However, coupling of 9 with 4-methoxyphenyl 4,6-0-benzylidene-beta-D-glucopyranoside (27) selectively gave beta-(1 --> 3)-linked tetrasaccharide 28. Simple chemical transformation of the tetrasaccharide 28 gave acylated tetrasaccharide trichloroacetimidate 29. Coupling of 29 with lauryl (I --> 6)-linked disaccharide 26 with 3-OH gave beta-(I --> 3)-linked hexasaccharide 30 as the major product. Bioassay showed that in combination with the chemotherapeutic agent cyclophospamide (CPA), the hexaose 18 at a dose of 0.5-1 mg/kg substantially increased the inhibition of S 180 for CPA, but decreased the toxicity caused by CPA. Some of these oligosaccharides also inhibited U-14 noumenal tumor in mice effectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00118-4

文献信息

• Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose
  作者：Shinkiti Koto、Naohiko Morishima、Sonoko Shichi、Hisamitsu Haigoh、Motoko Hirooka、Mitsuko Okamoto、Takashi Higuchi、Koichi Shimizu、Yosuke Hashimoto、Terumi Irisawa、Hidehiro Kawasaki、Yasushi Takahashi、Masayo Yamazaki、Yoko Mori、Keiko Kudo、Takako Ikegaki、Sonoe Suzuki、Shonosuke Zen

  DOI：10.1246/bcsj.65.3257

  日期：1992.12

  reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated. The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1→2)-linked biosyl donor undergo α-condensation. Several new linear trisaccharides were obtained via debenzylation

  D-吡喃葡萄糖的 2-、3-、4-和 6-OH 基团与葡萄糖二糖的七-O-苄基衍生物的脱水糖基化（OD-吡喃葡萄糖基-（1→n）-D-吡喃葡萄糖；n = 2， 3、4 或 6) 和乳糖，在对硝基苯磺酰氯、三氟甲磺酸银和三乙胺的三元混合物在二氯甲烷中的存在下表明反应的选择性取决于异头构型和与还原三苄基葡萄糖的连接位置非还原性四苄基葡萄糖残基的部分和要糖基化的 OH 基团的类别。使用对硝基苯磺酰氯、三氟甲磺酸银、N,N-二甲基乙酰胺和三乙胺的四元混合物使除 β(1→2)-连接的生物基供体以外的所有物质都发生 α-缩合。