2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride | 101966-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride
• 英文别名: 1-fluoro-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-galactopyranose；2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl fluoride；β-tetrabenzylgalactosyl fluoride；(2S,3R,4S,5S,6R)-2-fluoro-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 101966-50-1
• 化学式: C₃₄H₃₅FO₅
• 分子量: 542.647
• InChiKey: QNXIKNZDQVSBCO-BWNLSPMZSA-N

物化性质

• 沸点：
  639.4±55.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride 在 四丁基氟化铵 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2S,3S,4R)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-(tetracosanoylamino)nonane-3,4-diol
  参考文献：
  名称：

  Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH

  摘要：

  The phytosphingosine-containing alpha-galactosylceramides (alpha-GalCers), KRN7000 and OCH, have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 family of antigen presenting proteins. Evidence from KRN7000 stimulation of NKT cells suggests that alpha-GalCers may have applications in the treatment or prevention of a range of viral, bacterial, and autoimmune conditions. Moreover, OCH, a truncated analogue of KRN7000, appears to induce a T(H)2 bias, which could have implications for the treatment of autoimmune and inflammatory conditions. We have prepared the direct sphinganine-containing analogues of KRN7000 and OCH, 1 and 2, and found them to be comparable in activity to the parent compounds in inducing the release of IL-2, IL-4, and IFN gamma. In addition, compound 2 leads to a cytokine bias similar to that seen with OCH. This is significant because sphinganines are more easily accessed than phytosphingosines, which should facilitate SAR studies.

  DOI：

  10.1021/jo051147h
• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 在 四丁基氟化铵 、 二甲基二环氧乙烷 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride
  参考文献：
  名称：

  2-Deoxy-disaccharide approach to natural and unnatural glycosphingolipids synthesis

  摘要：

  2-Deoxy-disaccharides were easily converted into glycosylphytosphingosines, as new and efficient precursors of natural and unnatural glycosphingolipids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00366-9

文献信息

• Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
  作者：Sungjin Kim、Yaroslav Khomutnyk、Anton Bannykh、Pavel Nagorny

  DOI：10.1021/acs.orglett.0c03915

  日期：2021.1.1

  glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%–97%, and it was applied in continuous flow to accomplish fluorination on an

  本研究描述了一种使用六氟化硫 (VI) 作为廉价且安全的氟化剂和 4,4'-二甲氧基二苯甲酮作为易于获得的有机光催化剂光催化生成糖基氟的新方法。这种温和的方法用于生成 16 种不同的糖基氟化物，包括具有酸和碱不稳定官能团的底物，产率为 43%–97%，并以连续流方式应用，以 7.7 g 的规模和 93% 的产率完成氟化.
• Direct <i>C</i>-Glycosylation of Organotrifluoroborates with Glycosyl Fluorides and Its Application to the Total Synthesis of (+)-Varitriol
  作者：Jing Zeng、Seenuvasan Vedachalam、Shaohua Xiang、Xue-Wei Liu

  DOI：10.1021/ol102473k

  日期：2011.1.7

  C-glycosides via BF3·Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

  据报道，通过BF 3 ·Et 2 O促进了有机三氟硼酸酯和糖基氟化物的偶联，采用了温和，立体选择性和快速的方法访问炔基和烯基C-糖苷。该方法的应用通过仅七个步骤的简明有效的全合成（+）-varitriol进一步得到了证明。
• Synthesis of propargyl C-glycosides using allenyltributylstannane
  作者：Kit L. Chan、Gregory S. Coumbarides、Sirajul Islam、Peter B. Wyatt

  DOI：10.1016/j.tetlet.2004.11.040

  日期：2005.1

  Protected propargyl C-glycosides have been prepared by activation of the anomeric centres of 2,3,4,6-tetra-O-benzyl- derivatives of d-glucose and d-galactose, followed by treatment with allenyltributylstannane in the presence of Lewis-acid. Activation was by formation of the anomeric acetates, trichloroacetimidates or fluorides; boron trifluoride etherate and trimethylsilyl trifluoromethanesulfonate

  通过活化d-葡萄糖和d-半乳糖的2,3,4,6-四-O-苄基衍生物的异头中心，然后在Lewis-存在下用烯丙基三丁基锡烷处理来制备受保护的炔丙基C-糖苷。酸。活化是通过形成异头的乙酸盐，三氯乙亚氨酸盐或氟化物来进行的。三氟化硼醚化物和三甲基甲硅烷基三氟甲磺酸盐是特别有效的路易斯酸。尝试对1,2,3,4,6-penta- O-乙酰基-d-葡萄糖进行类似的反应导致C-2乙酸酯基团参与并形成3,4,6-tri- O-乙酰基-d-葡萄糖1,2- O- [1-（丙-2-炔基）亚乙基]-α-d-吡喃葡萄糖。
• Protic Acid Catalyzed Stereoselective Glycosylation Using Glycosyl Fluorides
  作者：Hideki Jona、Hiroki Mandai、Warinthorn Chavasiri、Kazuya Takeuchi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.75.291

  日期：2002.2

  A catalytic and stereoselective glycosylation of various glycosyl acceptors, such as methyl glycosides, thioglycosides, or a disarmed glycosyl fluoride, with benzyl-protected armed glycosyl fluoride was successfully carried out by using various protic acids in the presence of MS 5A. In the cases when trifluoromethanesulfonic acid (TfOH) or perchloric acid (HClO4) was used in diethyl ether (Et2O), α-glycosides

  在 MS 5A 存在下，使用各种质子酸成功地进行了各种糖基受体（如甲基糖苷、硫糖苷或脱臂糖基氟）与苄基保护的武装糖基氟的催化和立体选择性糖基化。在三氟甲磺酸 (TfOH) 或高氯酸 (HClO4) 用于乙醚 (Et2O) 的情况下，主要产物为 α-糖苷，而当四（五氟苯基）硼酸 [HB(C6F5) )4] 用于三氟甲基苯 (BTF)-新戊腈 (tBuCN) = 5:1 的混合溶剂中。这种糖基化的立体选择性受催化剂抗衡阴离子的性质以及溶剂的性质控制。还，
• Chemoselective glycosylations of sterically hindered glycosyl acceptors
  作者：Richard Geurtsen、Geert-Jan Boons

  DOI：10.1016/s0040-4039(02)02334-1

  日期：2002.12

  Unexpected intermolecular aglycon transfer in chemoselective glycosylations between activated thioglycosyl donors and deactivated thioglycosyl acceptors could be avoided by employing a glycosyl acceptor that has a bulky anomeric dicyclohexylmethanethio group. The methodology was applied to the synthesis of a protected fragment of an oligosaccharide released from the jelly coat glycoprotein of X. leavis

  通过使用具有庞大的异头二环己基甲硫基的糖基受体，可以避免活化的硫糖基供体和失活的硫糖基受体之间在化学选择性糖基化过程中发生意外的分子间糖苷配基转移。该方法适用于从X.leavis的果冻外壳糖蛋白释放的保护寡糖片段的合成。