Thioacetic acid S-[(2R,3R,4S,5R)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester | 198012-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Thioacetic acid S-[(2R,3R,4S,5R)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester
• CAS: 198012-19-0
• 化学式: C₃₆H₄₉NO₇SSi
• 分子量: 667.939
• InChiKey: XTNUTPKYKUKFAT-KXCACMGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  46.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  103.32
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Thioacetic acid S-[(2R,3R,4S,5R)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester 在 草酰氯 、 氨 、 sodium 、 二甲基亚砜 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 15.0h， 生成 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-4-yl ester
  参考文献：
  名称：

  UDP-N-acetyl-5-thio-galactosamine is a substrate of lactose synthase

  摘要：

  Uridine 5'-(N-acetyl-5-thio-galactosaminyl diphosphate) (UDP-5SGalNAc) was synthesized from an N-acetylgalactosamine derivative via ring opening-recyclization approach. UDP-5SGalNAc was active as a donor substrate for lactose synthase, the complex of galactosyltransferase and lactalbumin, giving the disaccharide mimic (5SGalNAc beta[1-->4]GlcNAc) which has a sulfur in the ring of the non-reducing sugar. The initial rate of the formation of the disaccharide mimic was 0.23% that for the natural disaccharide (GalNAc beta[1-->4]GlcNAc). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10009-9
• 作为产物：
  描述：

  (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-ylamine 在 二甲基溴化硼 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 Thioacetic acid S-[(2R,3R,4S,5R)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester
  参考文献：
  名称：

  UDP-N-acetyl-5-thio-galactosamine is a substrate of lactose synthase

  摘要：

  Uridine 5'-(N-acetyl-5-thio-galactosaminyl diphosphate) (UDP-5SGalNAc) was synthesized from an N-acetylgalactosamine derivative via ring opening-recyclization approach. UDP-5SGalNAc was active as a donor substrate for lactose synthase, the complex of galactosyltransferase and lactalbumin, giving the disaccharide mimic (5SGalNAc beta[1-->4]GlcNAc) which has a sulfur in the ring of the non-reducing sugar. The initial rate of the formation of the disaccharide mimic was 0.23% that for the natural disaccharide (GalNAc beta[1-->4]GlcNAc). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10009-9