pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: (4aR,6R,7R,8R,8aS)-7-azido-6-pent-4-enoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• 化学式: C₁₈H₂₃N₃O₅
• 分子量: 361.398
• InChiKey: VJPLPFZTOGQOPA-DBISQMLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	pent-4-enyl 2-azido-2-deoxy-α,β-D-glucopyranoside	——	C11H19N3O5	273.289
  2-叠氮基-2-脱氧-D-吡喃葡萄糖1,3,4,6-四乙酸酯	1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose	171032-74-9	C14H19N3O9	373.32
  ——	2-azido-2-deoxy-D-glucose	56883-39-7	C6H11N3O5	205.17

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-β-D-glucopyranoside 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 水 、 臭氧 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 38.0h， 生成 3-formylpropyl 2-deoxy 2-N-acetyl 3-O-(β-D-glucopyranosyluronate)-β-D-glucopyranoside
  参考文献：
  名称：

  Design and synthesis of hyaluronan-mimetic gemini disaccharides

  摘要：

  An efficient strategy has been designed for the preparation of synthetic mimics of hyaluronan (RA, 1) and its dimerized (Gemini) disaccharides (2a,b) via n-pentenyl glycoside formation. Construction of the target molecules was achieved through a combination of protection/deprotection protocols, imidate glycosylation methodology followed by ozonolysis, and reductive amination. These tailored synthetic mimics could act as versatile building blocks with therapeutic applications in tissue engineering, treatment of cancer and as drug delivery agents. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01567-3
• 作为产物：
  描述：

  2-叠氮基-2-脱氧-D-吡喃葡萄糖1,3,4,6-四乙酸酯 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 乙酸肼 、 potassium carbonate 、 (+)-10-camphorsulfonic acid 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.75h， 生成 pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Design and synthesis of hyaluronan-mimetic gemini disaccharides

  摘要：

  An efficient strategy has been designed for the preparation of synthetic mimics of hyaluronan (RA, 1) and its dimerized (Gemini) disaccharides (2a,b) via n-pentenyl glycoside formation. Construction of the target molecules was achieved through a combination of protection/deprotection protocols, imidate glycosylation methodology followed by ozonolysis, and reductive amination. These tailored synthetic mimics could act as versatile building blocks with therapeutic applications in tissue engineering, treatment of cancer and as drug delivery agents. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01567-3

文献信息

• Design and synthesis of hyaluronan-mimetic gemini disaccharides
  作者：Suri S Iyer、Shyam M Rele、S Baskaran、Elliot L Chaikof

  DOI：10.1016/s0040-4020(02)01567-3

  日期：2003.1

  An efficient strategy has been designed for the preparation of synthetic mimics of hyaluronan (RA, 1) and its dimerized (Gemini) disaccharides (2a,b) via n-pentenyl glycoside formation. Construction of the target molecules was achieved through a combination of protection/deprotection protocols, imidate glycosylation methodology followed by ozonolysis, and reductive amination. These tailored synthetic mimics could act as versatile building blocks with therapeutic applications in tissue engineering, treatment of cancer and as drug delivery agents. (C) 2003 Elsevier Science Ltd. All rights reserved.