(4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol | 753502-54-4

• 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: (4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 753502-54-4
• 化学式: C₂₁H₃₀O₆
• 分子量: 378.466
• InChiKey: ZAADEURCGNAVNL-GQUPQBGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以97%的产率得到isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and acid catalyzed hydrolysis of B2,5 type conformationally constrained glucopyranosides: incorporation into a cellobiose analogue

  摘要：

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides, restrained in a conformation close to B-2,B-5 via an oxymethylene bridge have been synthesized. These four glucopyranosides were found to be hydrolyzed at similar rates, close to those observed for the parent unconstrained glucosides. In such derivatives, either alpha or beta, the exocyclic cleaved bond is synperiplanar to an endocyclic oxygen lone pair. This conformationally locked glucopyranosyl moiety was also incorporated into a disaccharide, affording a conformationally restrained cellobiose analogue which was assayed against various glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.009
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 sodium 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 (4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
  参考文献：
  名称：

  Synthesis and acid catalyzed hydrolysis of B2,5 type conformationally constrained glucopyranosides: incorporation into a cellobiose analogue

  摘要：

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides, restrained in a conformation close to B-2,B-5 via an oxymethylene bridge have been synthesized. These four glucopyranosides were found to be hydrolyzed at similar rates, close to those observed for the parent unconstrained glucosides. In such derivatives, either alpha or beta, the exocyclic cleaved bond is synperiplanar to an endocyclic oxygen lone pair. This conformationally locked glucopyranosyl moiety was also incorporated into a disaccharide, affording a conformationally restrained cellobiose analogue which was assayed against various glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.009