phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside | 139608-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-((Benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate；[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 139608-36-9
• 化学式: C₂₅H₂₈O₈S
• 分子量: 488.559
• InChiKey: CHXRTDPWHZFMIJ-MQZWXTIWSA-N

物化性质

• 沸点：
  573.2±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside 在 guanidinium nitrate 、 胍 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 以99%的产率得到phenyl 6-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  胍/硝酸胍; 一种温和的选择性O-脱乙酰基试剂，可保持N -Troc基团完好无损

  摘要：

  用甲醇胍/硝酸胍的甲醇溶液处理O-乙酰基保护的糖可除去乙酰基（分离产率为91–99％），而不会影响其他保护基。除去O-苯甲酰基需要更长的反应时间。在这些弱碱性反应条件下，2,2,2-三氯乙氧羰基氨基（N -Troc）基团的稳定性特别有价值。

  DOI：

  10.1016/s0040-4039(97)00105-6
• 作为产物：
  描述：

  苯硫酚 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 D(+)-10-樟脑磺酸 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Lewis X-O -Core-1苏氨酸的合成：O-连接的Lewis X糖肽的结构单元

  摘要：

  LewisX（LeX）是一种分支的三糖Galβ1→4（Fucα1→3）GlcNAc，在许多细胞表面糖蛋白上表达，在先天性和适应性免疫应答中起关键作用。然而，携带LeX的糖肽的有效合成仍然是LeX决定簇结构功能研究的主要限制。在这里我们报告了使用区域选择性的1-苯亚磺酰基哌啶/三氟甲磺酸酐促进的[3 + 2]糖基化的LeX五糖1的总合成。Fmoc-苏氨酸氨基酸的存在促进了五糖在固相肽合成中的掺入，提供了通往多种O-连接的LeX糖肽的途径。所描述的方法广泛适用于合成多种复杂的糖肽，这些糖肽包含O-连接的LeX或唾液酸化的LewisX（sLeX）。

  DOI：

  10.1016/j.carres.2017.10.002

文献信息

• Use of dichlorophthaloyl (DCPhth) group as an amino protecting group in oligosaccharide synthesis
  作者：Matthias Lergenmüller、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0040-4020(97)10377-5

  日期：1998.2

  As an alternative to phthaloyl (Phth) group, 4,5-dichlorophthaloyl (DCPhth) group was investigated as an amino protecting group to prove it to be useful for the synthesis of β-glycosides of 2-acetamido-2-deoxy glucose (GlcNAc). DCPhth was introduced onto the C-2 nitrogen of glucosamine to give 2, which was further transformed into mono- and di- and trisaccharide derivatives which constitute basic structural

  作为邻苯二甲酰基（Phth）基团的替代品，研究了4,5-二氯邻苯二甲酰基（DCPhth）基团作为氨基保护基，证明其可用于合成2-乙酰氨基-2-脱氧葡萄糖（GlcNAc）的β-糖苷。 ）。将DCPhth引入到葡萄糖胺的C-2氮上，得到2进一步转化成构成天冬酰胺连接的糖蛋白寡糖的基本结构单元的单糖，二糖和三糖衍生物。DCPhth基团在保护基操作（例如脱乙酰基，苄基化，苄基化）和路易斯酸，银盐和碘鎓离子促进的糖基化的标准条件下证明具有足够的稳定性。通过在乙醇溶剂中使用乙二胺，在对Phth进行脱保护所需的实质上较温和的条件下，顺利地除去DCPhth基团。
• : A mild reagent for the regioselective reductive ring opening of benzylidene acetals in carbohydrates
  作者：Lu Jiang、Tak-Hang Chan

  DOI：10.1016/s0040-4039(97)10599-8

  日期：1998.1

  is an effective reagent to reductively cleave 4,6-O-benzylidene acetals of various hexopyranosides to the corresponding 4-O-benzyl ethers. 4,6-O-Isopropylidene acetals can be similarly cleaved. Common protecting groups are stable to the reaction conditions.

  是一种有效的试剂，用于将各种六吡喃糖苷的4,6-O-亚苄基缩醛还原为相应的4-O-苄基醚。可以类似地裂解4，6-O-异亚丙基缩醛。常见的保护基对反应条件是稳定的。
• Iodine Monochloride/Silver Trifluoromethanesulfonate (ICl/AgOTf) as a Convenient Promoter System for <i>O</i>-Glycoside Synthesis
  作者：Teddy Ercegovic、Andreas Meijer、Göran Magnusson、Ulf Ellervik

  DOI：10.1021/ol015547c

  日期：2001.3.1

  The novel promoter system iodine monochloride/silver trifluoromethanesulfonate (ICl/AgOTf) was evaluated with various thioglycoside donors and saccharide acceptors, and O-glycosides were obtained in 46-82% yield. Several practical advantages of the ICl/AgOTf system over known promoter systems were observed, such as convenient handling of the reagents and absence of byproducts related to N-succinimide

  用各种硫代糖苷供体和糖受体评估了新型的启动子系统一氯化碘/三氟甲磺酸银（IC1 / AgOTf），并以46-82％的产率获得了O-糖苷。观察到了ICl / AgOTf系统相对于已知启动子系统的一些实际优点，例如方便的试剂处理和不存在与N-琥珀酰亚胺有关的副产物。
• A High Yielding Chemical Synthesis of Sialyl Lewis x Tetrasaccharide and Lewis x Trisaccharide; Examples of Regio- and Stereodifferentiated Glycosylations
  作者：Ulf Ellervik、Göran Magnusson

  DOI：10.1021/jo981203x

  日期：1998.12.1

  Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-n-glucopyranoside (8) with the donor phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-beta-D-galactopyranoside (11) gave the lactosamine derivative 14, which was fucosylated with the donor 15 to give the Le(x) trisaccharide glycoside 2 after deprotection. Regioselective sialylation of the partially protected Le(x) trisaccharide triol 24 with the sialyl donor 25 gave, after deprotection, the SLe(x) tetrasaccharide glycoside 1. The overall yields of 2 and 1 from the monosaccharide starting materials 8, 11, 15, and 25 were 56% and 29%, respectively. In contrast to the virtually complete regio- and stereoselective galactosylation of 8, fucosylation with the benzyl-protected donor 15 gave the corresponding 1-->3- and 1-->4-linked disaccharides in a ratio of 3.6:1 (highly stereo- but not regioselective glycosylation), whereas fucosylation with acetyl-protected donor 18 gave a 2.2:1 beta/alpha-mixture of 4-O-linked disaccharides (highly regio- but not stereoselective glycosylation).
• Total synthesis of a unique tetrasaccharide present in the human clotting factor IX and mammalian Notch 1 receptor
  作者：Chinmoy Mukherjee、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2009.02.003

  日期：2009.3

  The Synthesis Of a unique tetrasaccharide linked to the serine 61 of human clotting factor IX through an alpha-L-fucose residue has been achieved for the first time in excellent yield. All glycosylation and protecting group manipulation steps are high yielding and reproducible for a scale-Lip preparation. A sequential glycosylation strategy has been used to assemble suitably protected monosaccharide synthons for the preparation of the target tetrasaccharide. (c) 2009 Elsevier Ltd. All rights reserved.