| 640722-41-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 640722-41-4
• 化学式: C₅₀H₄₈O₁₄S
• 分子量: 904.989
• InChiKey: CRCCDECSJSMKSC-ULUJDMCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  65.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  171.58
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Synthesis of β-d-glucose oligosaccharides from Phytophthora parasitica

  摘要：

  The glucohexaose, beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-(3-D-Glcp-(1 --> 6)]-(3-D-Glcp-(1 --> 3)-o-Glcp, was synthesized as its allyl glycoside via 3+3 strategy. The trisaccharide donor, 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-(3-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (11), was obtained by 3-selective coupling of isopropyl 4,6-O-benzylidene-1-thio-(3-D-glucopyranoside (2) with 2,3,4,6-tetra-O-benzoyl-(3-D-glucopyranosyl-(1 3)-2-O-acetyl-4,6-O-benzylidene-alpha-D-glucopyranosyl trichloroacetimidate (6), followed by hydrolysis, acetylation, dethiolation, and trichloroacetimidation. Meanwhile, the trisaccharide acceptor, allyl 2,3,4,6-tetra-O-benzoyl-(3-D-glucopyranosyl-(1 --> 3)-2-O-acetyl(3-D-glucopyranosyl-(1 3)-4,6-di-O-acetyl-2-O-benzoyl-alpha-D-glucopyranoside (14), was prepared by coupling of allyl 4,6-di-Oacetyl-2-O-benzoyl-alpha-D-glucopyranoside (12) with 6, followed by debenzylidenation. Condensation of 14 with 11, followed by deacylation, gave the target hexaoside. A (3-(1 ->3)-linked tetrasaccharide 29 was also synthesized with methyl 2-O-benzoyl-4,6-0benzylidene-(3-D-glucopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-(3-D-glucopyranoside (25) as the acceptor and acylated (3-(1 3)-linked disaccharide 21 as the donor. 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.004
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 、 isopropyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到
  参考文献：
  名称：

  Synthesis of β-d-glucose oligosaccharides from Phytophthora parasitica

  摘要：

  The glucohexaose, beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-(3-D-Glcp-(1 --> 6)]-(3-D-Glcp-(1 --> 3)-o-Glcp, was synthesized as its allyl glycoside via 3+3 strategy. The trisaccharide donor, 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-(3-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (11), was obtained by 3-selective coupling of isopropyl 4,6-O-benzylidene-1-thio-(3-D-glucopyranoside (2) with 2,3,4,6-tetra-O-benzoyl-(3-D-glucopyranosyl-(1 3)-2-O-acetyl-4,6-O-benzylidene-alpha-D-glucopyranosyl trichloroacetimidate (6), followed by hydrolysis, acetylation, dethiolation, and trichloroacetimidation. Meanwhile, the trisaccharide acceptor, allyl 2,3,4,6-tetra-O-benzoyl-(3-D-glucopyranosyl-(1 --> 3)-2-O-acetyl(3-D-glucopyranosyl-(1 3)-4,6-di-O-acetyl-2-O-benzoyl-alpha-D-glucopyranoside (14), was prepared by coupling of allyl 4,6-di-Oacetyl-2-O-benzoyl-alpha-D-glucopyranoside (12) with 6, followed by debenzylidenation. Condensation of 14 with 11, followed by deacylation, gave the target hexaoside. A (3-(1 ->3)-linked tetrasaccharide 29 was also synthesized with methyl 2-O-benzoyl-4,6-0benzylidene-(3-D-glucopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-(3-D-glucopyranoside (25) as the acceptor and acylated (3-(1 3)-linked disaccharide 21 as the donor. 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.004

文献信息

• Synthesis of an α-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6
  作者：Aixiao Li、Fanzuo Kong

  DOI：10.1016/j.carres.2004.07.026

  日期：2004.10

  A hexasaccharide, beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->2)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->2)]-D-Glcp, the alpha-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6, was synthesized as its methyl glycoside. Condensation of fully benzoylated alpha-D-glucopyranosyl trichloroacetimidate (1) with isopropyl 4,6-O-benzylid,ene-1-thio-beta-D-glucopyranoside (2) selectively furnished (1-->3)-linked disaccharide 3, and subsequent 2-O-acetylation, desulfation, and trichloroacetimidate formation afforded the disaccharide donor 6. Meanwhile, selective 3-O-coupling of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (8) with 3-O-allyl-2,4,6-tri-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (7), followed by coupling with 1 gave the trisaccharide 10. Removal of the benzylidene group of 10, benzoylation, and deallylation produced the trisaccharide acceptor 12. Condensation of 12 with 6 yielded a pentasaccharide mixture 13 with (3 and a isomers in a ratio of 2:1. Removal of the benzylidene group of 13, followed by benzoylation gave the pentasaccharide mixture 14. Selective 2"'-deacetylation of the isolated beta-linked 14 beta with MeCOCl/MeOH/CH2Cl2 did not give the expected pentasaccharide acceptor, and serious decomposition occurred, indicating a large steric hindrance at C-2"'. Alternatively, 2,3-di-O-glycosylation of allyl 4,6-O-benzylidene-beta-D-glucopyranoside (21) with 1 gave 22, then deallylation and trichloroacetimidate formation afforded the trisaccharide donor 24. Condensation of 12 with 24 furnished only the alpha-linked hexasaccharide 25, and its deprotection gave the free hexaoside 27. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of 3,6‐Branched β‐<scp>d</scp>‐Glucose Oligosaccharides
  作者：Youlin Zeng、Fanzuo Kong

  DOI：10.1081/car-120026599

  日期：2003.12.31

  A glucohexasaccharide, beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta(..)D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp was synthesized as its 4-methoxyphenyl glycosidevia 2 + 2 + 2 strategy with benzylidenated glucose mono- and disaccharides as the key intermediates.