1,2,3,6-tetra-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranose | 118918-81-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,6-tetra-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranose
• 英文别名: 1,2,3,6-tetra-O-acetyl-4-thio-α-D-galactopyranoside；[(2R,3S,4R,5R,6R)-4,5,6-triacetyloxy-3-acetylsulfanyloxan-2-yl]methyl acetate
• CAS: 118918-81-3
• 化学式: C₁₆H₂₂O₁₀S
• 分子量: 406.411
• InChiKey: AITRPFYRUORORI-SUJAAXHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranose 在 palladium on activated charcoal 正丁基锂 、 三正丁胺 、 1,4-环己二烯 、 sodium acetate 、 溴化钛(IV) 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.58h， 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 2,3,6-Tri-O-benzyl-4-O-triflyl-α-D-glucopyranoside 在 三氯化铁 作用下， 以 丁酮 为溶剂， 反应 49.5h， 生成 1,2,3,6-tetra-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranose
  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

文献信息

• A convenient synthesis of 4-thio-D-galactofuranose
  作者：Oscar Varela、Daniel Cicero、Rosa M. De Lederkremer

  DOI：10.1021/jo00269a025

  日期：1989.4
• VARELA, OSCAR;CICERO, DANIEL;DE, LEDERKREMER ROSA M., J. ORG. CHEM., 54,(1989) N, C. 1884-1890
  作者：VARELA, OSCAR、CICERO, DANIEL、DE, LEDERKREMER ROSA M.

  DOI：——

  日期：——
• Thiosugar nucleotide analogues: synthesis of uridine 5′-(2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-d-galactopyranosyl diphosphate)
  作者：Jordan Elhalabi、Kevin G Rice

  DOI：10.1016/s0008-6215(01)00228-2

  日期：2001.10

  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.