乙基-2,6-二-氧-苯甲酰基-3,4-氧-异丙叉-Β-D-硫代吡喃半乳糖苷 | 210093-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙基-2,6-二-氧-苯甲酰基-3,4-氧-异丙叉-Β-D-硫代吡喃半乳糖苷
• 英文名称: ethyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
• 英文别名: ethyl 2,6-Di-O-benzoyl-3,4-O-isopropylidene-β-D-galactothiopyranoside；((3AS,4R,6S,7R,7aS)-7-(benzoyloxy)-6-(ethylthio)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)methyl benzoate；[(3aS,4R,6S,7R,7aS)-7-benzoyloxy-6-ethylsulfanyl-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
• CAS: 210093-48-4
• 化学式: C₂₅H₂₈O₇S
• 分子量: 472.559
• InChiKey: SUZDTUKXUGUOQS-ZTGMJEERSA-N

物化性质

• 沸点：
  585.7±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙基-2,6-二-氧-苯甲酰基-3,4-氧-异丙叉-Β-D-硫代吡喃半乳糖苷 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 二正丁基氧化锡 、 DMTST 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.75h， 生成 hexadecyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharides Designed to form Micelles, Corresponding to Structures Found in Ovarian Cyst Fluid

  摘要：

  The syntheses of alpha-D-GlcpNAc-(1-->4)-beta-D-Galp-(1-->4)-beta-D-GlcNAc-(1-->O)-(CH2)(15)CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromo-derivative 18. For the synthesis of disaccharide beta-D-Galp-(1-->4)-D-GlcNAc, several differently protected glucosamine accepters were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the P-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.

  DOI：

  10.1080/07328300008544063
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 对甲苯磺酸 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 乙基-2,6-二-氧-苯甲酰基-3,4-氧-异丙叉-Β-D-硫代吡喃半乳糖苷
  参考文献：
  名称：

  Sarbajna, Sumita; Roy, Nirmolendu, Carbohydrate Research, 1998, vol. <1-2> 306, p. 400 - 408

  摘要：

  DOI：

文献信息

• Synthesis of a hexasaccharide corresponding to a porcine zona pellucida fragment that inhibits porcine sperm-oocyte interaction in vitro
  作者：Nynke M. Spijker、Cor A. Keuning、Mariska Hooglugt、Gerrit H. Veeneman、Constant A.A. van Boeckel

  DOI：10.1016/0040-4020(96)00225-6

  日期：1996.4

  The synthesis of hexasaccharide1, [Galβ(1-4)GlcNAc[6OSO3]β(1-3)Galβ(1-4)GlcNAcβ(1-3)Galβ(1-3)GalNAcα-O(CH2)3NH2], which corresponds to a porcine zona pellucida fragment that inhibits porcine sperm-oocyte interaction, is described. Compound1 was obtained from fully protected hexasaccharide2, which was in turn constructed from protected Galβ(1-3)GalNAc disaccharide5, containing an α-linked 3-azidopropyl

  六糖1，[Galβ（1-4）GlcNAc [6OSO 3 ]β（1-3）Galβ（1-4）GlcNAcβ（1-3）Galβ（1-3）GalNAcα-O（CH 2）3的合成描述了NH 2 ]，其对应于抑制猪精子-卵母细胞相互作用的猪透明带片段。化合物1是从完全保护的六糖2中获得的，而六糖2依次由保护的Galβ（1-3）GalNAc二糖5（包含一个与α连接的3-叠氮丙基间隔基）以及乳糖胺衍生物3和4构成。通过将硒代苯基糖苷偶联制备二糖3和46具有含有异头硫代乙基的糖基受体。NIS / TfOH促进了二糖4与5的偶联，得到29，通过选择性除去乙酰丙酰基将其转化为四糖受体30。用3的30进行糖基化，得到保护的六糖2。去除邻苯二甲酰亚胺基，乙酰化，然后选择性去除烯丙基和硫酸化，最后完全脱保护，得到六糖1。
• Synthesis of cancer-associated glycoantigens: stage-specific embryonic antigen 3 (SSEA-3)
  作者：Papapida Pornsuriyasak、Alexei V. Demchenko

  DOI：10.1016/j.carres.2006.03.041

  日期：2006.7

  The synthesis of the tumor-associated carbohydrate antigens SSEA-3 and Gb3 in a semi-convergent fashion using building blocks bearing a S-thiazolinyl (STaz) moiety is reported. Complete stereoselective control of a difficult alpha-(1 -> 4)-galactosylation and high overall yields were achieved. (c) 2006 Elsevier Ltd. All rights reserved.
• Acyl Transfer as a Problematic Side Reaction in Polymer-Supported Oligosaccharide Synthesis
  作者：Tomoo Nukada、Attila Berces、Dennis M. Whitfield

  DOI：10.1021/jo990712b

  日期：1999.12.1

  Under a wide variety of glycosylation conditions acyl transfer to the polymer support competed with glycoside formation, including the pivaloyl protecting group. As well as acyl transfer, many glycosylations also led to the formation of polymer-bound beta-1,2-linked oligomers of the donor. Using ethyl 2,6-di-O-pivaloyl-3,w4-O-isopropylidene-beta-D-galactothiopyranoside as donor under promotion of N-iodosuccinimide/silver trifluoromethanesulfonate in the presence of 2-methyl-2-butene, an 82% yield of glycoside was obtained along with pivaloylated polymer. Subsequent work showed that increasing the steric bulk about the alcoholic acceptor in conjunction with this 2-O-pivaloyl-protected glycosyl donor completely suppresses this side reaction, giving a nearly quantitative yield of glycoside. This contraintuitive approach of decreasing the reactivity of both the donor and the acceptor to minimize a side reaction is rationalized by assuming that the barrier to acyl transfer is more sensitive to the protecting groups than that of glycosylation. These developments led to a polymer-supported synthesis of the branch point trisaccharide of the group B type 1A Streptococcus capsular polysaccharide.