(2-methyl-5-tert-butylphenyl) 4,6-O-(p-methoxybenzylidene)-1-thia-α-D-mannopyranoside | 1442422-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methyl-5-tert-butylphenyl) 4,6-O-(p-methoxybenzylidene)-1-thia-α-D-mannopyranoside
• 英文别名: 2-methyl-5-tert-butylphenyl 4,6-O-p-methoxybenzylidine-1-thio-α-D-mannopyranoside
• CAS: 1442422-74-3
• 化学式: C₂₅H₃₂O₆S
• 分子量: 460.591
• InChiKey: JDBAPHMKEZDGCZ-POTYRQCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2-methyl-5-tert-butylphenyl) 4,6-O-(p-methoxybenzylidene)-1-thia-α-D-mannopyranoside 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 水 、 sodium hexamethyldisilazane 、 sodium hydride 、 二异丁基氢化铝 、 二正丁基氧化锡 、 二甲基亚砜 、 2-[N,正双(三氟甲烷烷磺酰)氨基]-5-氯吡啶 、 三氟乙酸 、 copper(II) oxide 、 copper dichloride 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 74.54h， 生成 i-propyl 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-6-thia-β-D-mannoheptopyranoside
  参考文献：
  名称：

  Improved methods for the stereoselective synthesis of mannoheptosyl donors and their glycosides: toward the synthesis of the trisaccharide repeating unit of the Campylobacter jejuni RM1221 capsular polysaccharide

  摘要：

  In view of the importance of 6-deoxymannoheptosides as structural units in the Campylobacter jejuni RM1221 capsular polysaccharide, the development of effective synthetic protocols for 4-O-6-S-alpha-cyanobenzylidene thio-o-mannoheptapyranoside donors carrying either 3-O-naphthylmethyl or 3-O-acetyl groups is described starting from D-mannose. In particular, tris(phenylthio)methyllithium is found to undergo highly stereoselective addition to a mannose-6-aldehyde in sharp contrast to the vinyl Grignard reagent whose reactions were essentially devoid of selectivity. A brief survey of coupling reactions with the two donors indicted the 3-O-acetyl system to be highly alpha-selective whereas the 3-O-naphthylmethyl congener was highly beta-selective indicating that the presence of the seventh carbon atom in these donors is not detrimental to coupling selectivity in either instance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.094
• 作为产物：
  描述：

  5-叔丁基-2-甲基苯硫酚 在 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2-methyl-5-tert-butylphenyl) 4,6-O-(p-methoxybenzylidene)-1-thia-α-D-mannopyranoside
  参考文献：
  名称：

  Improved methods for the stereoselective synthesis of mannoheptosyl donors and their glycosides: toward the synthesis of the trisaccharide repeating unit of the Campylobacter jejuni RM1221 capsular polysaccharide

  摘要：

  In view of the importance of 6-deoxymannoheptosides as structural units in the Campylobacter jejuni RM1221 capsular polysaccharide, the development of effective synthetic protocols for 4-O-6-S-alpha-cyanobenzylidene thio-o-mannoheptapyranoside donors carrying either 3-O-naphthylmethyl or 3-O-acetyl groups is described starting from D-mannose. In particular, tris(phenylthio)methyllithium is found to undergo highly stereoselective addition to a mannose-6-aldehyde in sharp contrast to the vinyl Grignard reagent whose reactions were essentially devoid of selectivity. A brief survey of coupling reactions with the two donors indicted the 3-O-acetyl system to be highly alpha-selective whereas the 3-O-naphthylmethyl congener was highly beta-selective indicating that the presence of the seventh carbon atom in these donors is not detrimental to coupling selectivity in either instance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.094

文献信息

• Highly convergent synthesis of a β-mannuronic acid alginate hexadecasaccharide
  作者：Dingyi Pan、Liangliang Zhang、Qingting Hua、You Yang

  DOI：10.1039/c9ob01254k

  日期：——

  Solution-phase synthesis of poly-β-mannuronic acids still remains unexplored. We report the first synthesis of a β-mannuronic acid alginate hexadecasaccharide representing the longest synthetic polymannuronic acid so far. The highly convergent synthetic approach provides a new avenue to access poly-β-mannuronic acids that can enable the biological evaluation of poly-β-mannuronic acids as potential

  聚-β-甘露糖醛酸的溶液相合成仍未探索。我们报道了迄今为止合成时间最长的β-甘露糖醛酸海藻酸酯十六烷基糖的首次合成。高度收敛的合成方法为获取聚β-甘露糖醛酸提供了一条新途径，可以使聚β-甘露糖醛酸作为潜在的治疗剂和疫苗进行生物学评估。