S-phenyl 3-O-benzyl-4,6-O-benzylidene-β-D-thiomannopyranoside | 848397-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-phenyl 3-O-benzyl-4,6-O-benzylidene-β-D-thiomannopyranoside
• 英文别名: phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-mannopyranoside
• CAS: 848397-74-0
• 化学式: C₂₆H₂₆O₅S
• 分子量: 450.555
• InChiKey: UHIVFVSDWCGRGZ-CNGGBCMRSA-N

物化性质

• 沸点：
  633.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  S-phenyl 3-O-benzyl-4,6-O-benzylidene-β-D-thiomannopyranoside 在 吡啶 、 三乙基硅烷 、 叠氮化四丁基铵 、 三氟乙酸 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.0h， 生成 phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  霍乱弧菌O43四糖重复单元的全合成

  摘要：

  霍乱弧菌是导致致命流行病——霍乱的病原体。不同霍乱弧菌菌株表面存在的聚糖被认为是潜在的候选疫苗。霍乱弧菌O43 的四糖重复单元 (RU) 装饰有较少探索的稀有脱氧氨基糖，如d-奎诺胺和d-维维糖胺，以及稀有氨基酸N-乙酰基-l-别苏氨酸。在此，我们详细报道了霍乱弧菌O43 四糖 RU 的全合成。在我们早期的尝试中，虽然三糖的一锅组装是成功的，但与完全功能化的d-维奥胺供体的最终偶联产率较低。成功的路线涉及使用 Fmoc 保护的d-维糖胺结构单元作为供体以及四糖的后期酰胺键形成。

  DOI：

  10.1021/acs.joc.3c02886
• 作为产物：
  描述：

  S-phenyl 4,6-O-benzylidene-β-D-thiomannopyranoside 、 溴甲苯 在 二正丁基氧化锡 、 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以81%的产率得到S-phenyl 3-O-benzyl-4,6-O-benzylidene-β-D-thiomannopyranoside
  参考文献：
  名称：

  全合成荧光假单胞菌O特异多糖的三糖重复单元BIM B-582

  摘要：

  报道了荧光假单胞菌BIM B-582的O-特异性多糖的三糖重复单元的第一全合成。这种高效的合成涉及连续1,2-顺式的糖基化包括β-升-rhamnosylation和α选择性稀有4-脱氧的耦合d -木糖-hexose作为关键步骤。合成的三糖在还原端配有一个氨基丙基接头，以便与蛋白质和微阵列结合，以进行进一步的免疫学研究。

  DOI：

  10.1021/acs.orglett.8b02669

文献信息

• 4,6-<i>O</i>-Benzylidene-Directed β-Mannopyranosylation and α-Glucopyranosylation:  The 2-Deoxy-2-fluoro and 3-Deoxy-3-fluoro Series of Donors and the Importance of the O2−C2−C3−O3 Interaction
  作者：David Crich、Linfeng Li

  DOI：10.1021/jo062294y

  日期：2007.3.1

  A series of 4,6-O-benzylidene-protected 2-O-benzyl-3-deoxy-3-fluoro- and 3-O-benzyl-2-deoxy-2-fluorogluco- and mannopyranosyl thioglycosides were synthesized and their coupling reactions with a series of alcohols, on preactivation with 1-benzenesulfinylpiperidine and trifluoromethanesulfonic anhydride, investigated. In all cases, the selectivities were lower than those observed with the corresponding simple 4,6-O-benzylidene 2,3-di-O-benzylgluco- and mannopyranosyl thioglycosides. This leads to the conclusion that the high beta-selectivity observed with 4,6-O-benzylidene 2,3-di-O-benzylmannopyranosyl donors under the same conditions is in large part derived from the compression of the O2-C2-C3-O3 torsion angle on going from the intermediate covalent glycosyl triflate to the oxacarbenium ion, as compared to the relaxation of this torsion angle in the gluco series.
• Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates
  作者：David Crich、Thomas K. Hutton、Abhisek Banerjee、Prasanna Jayalath、John Picione

  DOI：10.1016/j.tetasy.2004.11.032

  日期：2005.1

  A series of D-mannopyranosyl and L-rhamnopyranosyl thioglycosides; protected with electron-withdrawing non-participating protecting groups on O-2 have been prepared and investigated for their potential as beta-glycosyl donors. Both alpha- and beta-thioglycosides were investigated and the latter preferred on the grounds of enhanced stability at room temperature. A 2-O-nitro-L-rhamnosyl fluoride was also prepared and investigated. Moderate beta-selectivities were observed with some of these donors. With the more powerfully electron-withdrawing groups reduced donor reactivity leads to a requirement for higher reaction temperatures and reduced selectivities. Decomposition temperatures of the intermediate glycosyl triflates were determined by variable temperature NMR spectroscopy and generally correlate with the disarming propensity of the protecting group system. (C) 2004 Elsevier Ltd. All rights reserved.
• The methylsulfonylethoxymethyl (Msem) as a hydroxyl protecting group in oligosaccharide synthesis
  作者：Asghar Ali、Richard J.B.H.N. van den Berg、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D.C. Codée

  DOI：10.1016/j.tet.2010.06.007

  日期：2010.8

  The methylsulfonylethoxymethyl (Msem) is introduced as a base-labile, non-participating protecting group in carbohydrate chemistry. Conditions to introduce the Msem on primary and secondary alcohols are described. Removal of the Msem is best achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF), with or without a nucleophilic scavenger. Applicability of the Msem group is illustrated in the assembly of an all 1,3-cis-linked mannotrioside. (c) 2010 Elsevier Ltd. All rights reserved.