2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranosyl dibenzyl phosphate | 394212-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranosyl dibenzyl phosphate
• CAS: 394212-37-4
• 化学式: C₂₈H₃₃O₁₂PS
• 分子量: 624.603
• InChiKey: KDPJTOWGRIAKBX-VNFNVIIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranosyl dibenzyl phosphate 在 palladium on activated charcoal 三正丁胺 、 1,4-环己二烯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 uridine 5'-(2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranosyl diphosphate)
  参考文献：
  名称：

  Thiosugar nucleotide analogues: synthesis of uridine 5′-(2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-d-galactopyranosyl diphosphate)

  摘要：

  The synthesis of a novel uridine diphosphate galactose (UDP-Gal) analog, (UDP-2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-alpha -D-galactopyranose) (10) is described. Compound 10 contains a sulfur in the place of oxygen at the 4-position of the galactose moiety. Compound 10 represents a protected form of a novel sugar nucleotide analog that can potentially be used during chemoenzymatic synthesis to modify complex oligosaccharides. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00228-2
• 作为产物：
  描述：

  methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 盐酸 、 正丁基锂 、 sodium acetate 、 三氯化铁 、 溴化钛(IV) 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 丁酮 为溶剂， 反应 63.08h， 生成 2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranosyl dibenzyl phosphate
  参考文献：
  名称：

  Thiosugar nucleotide analogues: synthesis of uridine 5′-(2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-d-galactopyranosyl diphosphate)

  摘要：

  The synthesis of a novel uridine diphosphate galactose (UDP-Gal) analog, (UDP-2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-alpha -D-galactopyranose) (10) is described. Compound 10 contains a sulfur in the place of oxygen at the 4-position of the galactose moiety. Compound 10 represents a protected form of a novel sugar nucleotide analog that can potentially be used during chemoenzymatic synthesis to modify complex oligosaccharides. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00228-2