Acetic acid (3aS,4R,6R,7R,7aS)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester | 916453-33-3

• 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: Acetic acid (3aS,4R,6R,7R,7aS)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
• 英文别名: [(3aS,4R,6R,7R,7aS)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[(4-methoxyphenyl)-diphenylmethyl]sulfanyl-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
• CAS: 916453-33-3
• 化学式: C₄₇H₅₂O₇SSi
• 分子量: 789.077
• InChiKey: DWPXWPXZPMWAAL-ZERPUJLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.47
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aS,4R,6R,7R,7aS)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以84%的产率得到Acetic acid (3aS,4R,6R,7R,7aS)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-mercapto-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
  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
• 作为产物：
  描述：

  [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[(4-methoxyphenyl)-diphenylmethyl]sulfanyloxan-2-yl]methyl acetate 在 吡啶 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 Acetic acid (3aS,4R,6R,7R,7aS)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
  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