Thexyldimethylsilyl 3,4-O-isopropylidene-β-D-galactopyranoside | 176169-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Thexyldimethylsilyl 3,4-O-isopropylidene-β-D-galactopyranoside
• CAS: 176169-44-1
• 化学式: C₁₇H₃₄O₆Si
• 分子量: 362.539
• InChiKey: VDNHOABAYZTNBX-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 Thexyldimethylsilyl 3,4-O-isopropylidene-β-D-galactopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ((3aS,4R,6R,7R,7aS)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-dimethyl-(1,1,2-trimethyl-propyl)-silane 、 ((3aS,4R,6S,7R,7aS)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-dimethyl-(1,1,2-trimethyl-propyl)-silane
  参考文献：
  名称：

  Silyl Group Migration in 1-O-Silyl Protected Sugars-Convenient Synthesis of 2-O-Unprotected Sugars

  摘要：

  Reaction of 2-O-unprotected 1-O-silyl-protected D-glucose and D-galactose derivatives 5a-d with benzyl bromide in the presence of sodium hydride as the base afforded 1-O-benzyl 2-O-silyl derivatives 6a alpha/beta - 6d alpha/beta. Thus, prior to anomeric O-benzylation, trans-1,2-silyl group migration takes place. Ensuing removal of the 2-O-silyl group furnishes 2-O-unprotected compounds 8a alpha/beta - 8d alpha/beta, which are useful building blocks. More prone to 1-O-silyl group migration is mannose as shown for derivatives of 4,6-O-benzylidene-D-mannose 9. Cis-1,2- and cis-2,3-silyl group migrations affording compounds 15 and 13 were already observed on deacetylation of the thexyldimethylsilyl 2,3-di-O-acetyl derivative 12 beta under Zemplen conditions.

  DOI：

  10.1080/07328309608005442
• 作为产物：
  描述：

  Acetic acid (3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-tetrahydro-pyran-3-yl ester 在 sodium methylate 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 反应 42.0h， 生成 Thexyldimethylsilyl 3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Silyl Group Migration in 1-O-Silyl Protected Sugars-Convenient Synthesis of 2-O-Unprotected Sugars

  摘要：

  Reaction of 2-O-unprotected 1-O-silyl-protected D-glucose and D-galactose derivatives 5a-d with benzyl bromide in the presence of sodium hydride as the base afforded 1-O-benzyl 2-O-silyl derivatives 6a alpha/beta - 6d alpha/beta. Thus, prior to anomeric O-benzylation, trans-1,2-silyl group migration takes place. Ensuing removal of the 2-O-silyl group furnishes 2-O-unprotected compounds 8a alpha/beta - 8d alpha/beta, which are useful building blocks. More prone to 1-O-silyl group migration is mannose as shown for derivatives of 4,6-O-benzylidene-D-mannose 9. Cis-1,2- and cis-2,3-silyl group migrations affording compounds 15 and 13 were already observed on deacetylation of the thexyldimethylsilyl 2,3-di-O-acetyl derivative 12 beta under Zemplen conditions.

  DOI：

  10.1080/07328309608005442