ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside | 457931-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
• 英文别名: 4,6-O-benzylidene-3-O-tert-butyl-diphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside；[(2R,4aR,6R,7S,8S,8aR)-6-ethylsulfanyl-7-[(4-methoxyphenyl)methoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy-tert-butyl-diphenylsilane
• CAS: 457931-12-3
• 化学式: C₃₉H₄₆O₆SSi
• 分子量: 670.942
• InChiKey: QMFRAGLSCJVKKA-DTGQXANJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 27.17h， 生成 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1
• 作为产物：
  描述：

  4-甲氧基氯苄 在 咪唑 、 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 ethyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1

文献信息

• Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Amphoteric Glycolipid Analogues from the Porcine Nematode, Ascaris suum.
  作者：Isao Ohtsuka、Noriyasu Hada、Hiroko Ohtaka、Mutsumi Sugita、Tadahiro Takeda

  DOI：10.1248/cpb.50.600

  日期：——

  A novel amphoteric glycosphingolipid, cholinephosphoryl-(→6)-β-D-GlcpNAc-(1→3)-β-D-Manp-(1→4)-β-D-Glcp-(1→)-Cer, isolated from the porcine parasitic nematode, Ascaris suum, may be expected to be involved in host-parasite interactions. This glycosphingolipid analogue containing octyl residue in place of ceramide was synthesized as follows: The key reaction of this synthetic procedure is the formation of a intramolecular aglycon delivery (IAD) approach for β-selective mannosylation. Then, a coupling of phosphocholine group at the position C-6″ of 16 was attempted using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by reaction of the resulting cyclic phosphate intermediate with anhydrous trimethylamine to give 17. Subsequent debenzylation and debenzylidenation afforded target compound (2).

  从猪寄生线虫猪蛔虫(Ascaris suum)中分离得到一种新型两性糖神经鞘脂——胆碱磷酸基-(→6)-β-D-GlcpNAc-(1→3)-β-D-Manp-(1→4)-β-D-Glcp-(1→)-神经酰胺，可能参与宿主-寄生虫相互作用。含辛基残基替代神经酰胺的类似糖神经鞰脂合成步骤如下：该合成过程的关键反应是形成内酰胺输送(IAD)途径以实现β-选择性甘露糖化。然后，在16的C-6″位上尝试进行磷酸胆碱基的耦合，使用2-氯-2-氧-1,3,2-二氧磷杂环戊烷，随后与无水三甲胺反应，得到环状磷酸酯中间体17。接着经过去苄基化和去苄叉基化得到目标化合物(2)。
• Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids
  作者：Isao Ohtsuka、Noriyasu Hada、Mutsumi Sugita、Tadahiro Takeda

  DOI：10.1016/s0008-6215(02)00295-1

  日期：2002.11

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.