Ethyl 2,3,4-tri-O-benzoyl-1-thio-β-L-fucopyranoside | 116546-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2,3,4-tri-O-benzoyl-1-thio-β-L-fucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-4,5-dibenzoyloxy-6-ethylsulfanyl-2-methyloxan-3-yl] benzoate
• CAS: 116546-90-8
• 化学式: C₂₉H₂₈O₇S
• 分子量: 520.603
• InChiKey: MEWVDTRRQVNQMW-XZMALWCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Ethyl 2,3,4-tri-O-benzoyl-1-thio-β-L-fucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 四丁基溴化铵 、 copper(ll) bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Chemical and enzymatic synthesis of high-affinity selectin ligands

  摘要：

  Analogs of sialyl Lewis(x) have been synthesized chemically using donors of modified sialic acids. The sialic acids were obtained enzymatically by an aldolase reaction. The sLe(x) tetrasaccharides modified at C-2 of the GlcNAc moiety and at C-5 of the sialic acid residue were tested as inhibitors for E- and P-selectins. Up to 12-fold higher inhibitory potency was found for the lyse-derivative of sLeX compared to the parent compound. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00051-6
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 在 吡啶 、 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 Ethyl 2,3,4-tri-O-benzoyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of Guanosine 5′-(β-L-Fucopyranosyl)-Diphosphate Revisited

  摘要：

  It will be demonstrated that a successful synthesis of beta-L-fucopyranose-1-phosphate (2), a key intermediate in the preparation of guanosine 5'-(beta-L-fucopyranose)-diphosphate (1), strongly depends on the nature of the acyl protecting groups for the non-anomeric hydroxyl functions. Thus, the perbenzoylated, instead of peracetylated, alpha-L-fucopyranosyl trichloroacetimidate (11) or the corresponding ethyl beta-thiofucopyranoside proved to be a convenient starting compound for the preparation of 2. Further, condensation of N,N'-dicyclohexyl-4-morpholinecarboxamidinium guanosine 5'-morpholidophosphate with excess 2 gave the title compound without concomitant formation of bisguanosine-5'-diphosphate (16).

  DOI：

  10.1080/07328309608005678

文献信息

• An approach towards the synthesis of 1,2-trans glycosyl phosphates via iodonium ion assisted activation of thioglycosides
  作者：G.H. Veeneman、H.J.G. Broxterman、G.A.van der Marel、J.H.van Boom

  DOI：10.1016/0040-4039(91)80782-2

  日期：1991.10

  Phosphorylation of benzoylated ethyl 1,2-trans 1-thioglycosides with dibenzyl phosphate in the presence of NIS gave, after removal of all protecting groups, 1,2-trans glycosyl phosphates. The scope of the stereoselective method was demonstrated by the synthesis of GDP-fucose and the disaccharide α-d-Glcp-(1→3)-α-l-Rhap-1-PO4−.

  在除去所有保护基团后，在NIS存在下用磷酸二苄基酯对苯甲酰化的1,2-反式1-硫代1-硫代糖苷进行磷酸化，得到1,2-反式糖基磷酸酯。立体选择性方法的范围是由GDP-岩藻糖的合成，所述二糖α-d-GLC证实p（1→3）-α-L-鼠李糖- p -1-PO 4 - 。
• Baumann, Herbert; Jansson, Per-Erik; Kenne, Lennart, Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2229 - 2233
  作者：Baumann, Herbert、Jansson, Per-Erik、Kenne, Lennart

  DOI：——

  日期：——
• BAUMANN, HERBERT;ERBING, BERTIL;JANSSON, PER-ERIK;KENNE, LENNART, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N2, C. 2167-2178
  作者：BAUMANN, HERBERT、ERBING, BERTIL、JANSSON, PER-ERIK、KENNE, LENNART

  DOI：——

  日期：——
• BAUMANN, HERBERT;ERBING, BERTIL;JANSSON, PER-ERIK;KENNE, LENNART, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N2, C. 2145-2151
  作者：BAUMANN, HERBERT、ERBING, BERTIL、JANSSON, PER-ERIK、KENNE, LENNART

  DOI：——

  日期：——