(2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-tetrahydro-pyran | 916453-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-tetrahydro-pyran
• CAS: 916453-29-7
• 化学式: C₅₄H₅₂O₆S
• 分子量: 829.069
• InChiKey: DZHOGKOGVQXJSM-FOWBBQRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.42
• 重原子数：
  61.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-tetrahydro-pyran 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranose
  参考文献：
  名称：

  Exploring the Native Chemical Ligation Concept for Highly Stereospecific Glycosylation Reactions

  摘要：

  Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlled activating system. To explain the origin of stereoselective preference, an S(N)i mechanism was proposed and corroborated by computational calculations.

  DOI：

  10.1021/jo400020q
• 作为产物：
  描述：

  4-甲氧基三苯基氯甲烷 在 吡啶 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 生成 (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-tetrahydro-pyran
  参考文献：
  名称：

  MMTr as an efficient anomeric S-protecting group for the synthesis of glycosyl thiols

  摘要：

  The 4-monomethoxytrityl (MMTr) group was introduced in high yields to anomeric sulfhydryl functions using commercially available MMTrCl. Significantly, it is stable to a variety of reaction conditions, including acids and bases, and is removable under very mild acidic conditions, which are compatible with the presence of a number of other acid-labile hydroxyl protecting groups. The successful preparation of seven glycosyl thiols indicates that MMTr has potential application for the synthesis of complex 1-thiosugars. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.003