4-pentenyl 2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-β-D-mannopyranoside | 855271-00-0

• 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: 4-pentenyl 2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-β-D-mannopyranoside
• 英文别名: benzyl N-[(4aR,6R,7S,8R,8aS)-8-hydroxy-2,2-dimethyl-6-pent-4-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate
• CAS: 855271-00-0
• 化学式: C₂₂H₃₁NO₇
• 分子量: 421.491
• InChiKey: JTQPMASIPWEUDQ-USYVTKNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-pentenyl 2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-β-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.33h， 生成 1-adamantyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  α-N-Acetylmannosamine (ManNAc) Synthesis via Rhodium(II)-Catalyzed Oxidative Cyclization of Glucal 3-Carbamates

  摘要：

  Glucal 3-carbamates 1 and 7 underwent oxidative cyclization with iodobenzene diacetate or iodosobenzene in the presence of Rh-2(OAc)(4), providing mannosamine 2-N,3-O-oxazolidinones. With iodosobenzene, incorporation of 4-penten-1-ol provided a readily separable anomeric mixture of n-pentenyl glycosides, with the anomers exhibiting pronounced differences in reactivity as glycosyl donors. N-acylation of the sugar oxazolidinones led to a-selective glycosyl donors for the elaboration of various 2-mannosamine frameworks. Alternatively, the anomeric n-pentenyl glycosides of N-Cbz 2-mannosamine oxazolidinones were converted separately to oxazolidinone-opened derivatives 28 alpha and 28 beta. These served as stereoconvergent glycosyl donors, and the a-linked products were readily advanced to a variety of N-acetylmannosamine (ManNAc) frameworks, using an intramolecular O -> N acetyl transfer as the final step.

  DOI：

  10.1021/jo0500129
• 作为产物：
  描述：

  4,6-O-异亚丙基-D-葡萄糖醛 在 dirhodium tetraacetate 4-二甲氨基吡啶 、 lithium hydroxide 、 亚碘酰苯 、 4 A molecular sieve 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 4-pentenyl 2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-β-D-mannopyranoside
  参考文献：
  名称：

  α-N-Acetylmannosamine (ManNAc) Synthesis via Rhodium(II)-Catalyzed Oxidative Cyclization of Glucal 3-Carbamates

  摘要：

  Glucal 3-carbamates 1 and 7 underwent oxidative cyclization with iodobenzene diacetate or iodosobenzene in the presence of Rh-2(OAc)(4), providing mannosamine 2-N,3-O-oxazolidinones. With iodosobenzene, incorporation of 4-penten-1-ol provided a readily separable anomeric mixture of n-pentenyl glycosides, with the anomers exhibiting pronounced differences in reactivity as glycosyl donors. N-acylation of the sugar oxazolidinones led to a-selective glycosyl donors for the elaboration of various 2-mannosamine frameworks. Alternatively, the anomeric n-pentenyl glycosides of N-Cbz 2-mannosamine oxazolidinones were converted separately to oxazolidinone-opened derivatives 28 alpha and 28 beta. These served as stereoconvergent glycosyl donors, and the a-linked products were readily advanced to a variety of N-acetylmannosamine (ManNAc) frameworks, using an intramolecular O -> N acetyl transfer as the final step.

  DOI：

  10.1021/jo0500129

文献信息

• α-<i>N-</i>Acetylmannosamine (ManNAc) Synthesis via Rhodium(II)-Catalyzed Oxidative Cyclization of Glucal 3-Carbamates
  作者：Rena Bodner、Bridget K. Marcellino、Alexandra Severino、Abigail L. Smenton、Christian M. Rojas

  DOI：10.1021/jo0500129

  日期：2005.5.1

  Glucal 3-carbamates 1 and 7 underwent oxidative cyclization with iodobenzene diacetate or iodosobenzene in the presence of Rh-2(OAc)(4), providing mannosamine 2-N,3-O-oxazolidinones. With iodosobenzene, incorporation of 4-penten-1-ol provided a readily separable anomeric mixture of n-pentenyl glycosides, with the anomers exhibiting pronounced differences in reactivity as glycosyl donors. N-acylation of the sugar oxazolidinones led to a-selective glycosyl donors for the elaboration of various 2-mannosamine frameworks. Alternatively, the anomeric n-pentenyl glycosides of N-Cbz 2-mannosamine oxazolidinones were converted separately to oxazolidinone-opened derivatives 28 alpha and 28 beta. These served as stereoconvergent glycosyl donors, and the a-linked products were readily advanced to a variety of N-acetylmannosamine (ManNAc) frameworks, using an intramolecular O -> N acetyl transfer as the final step.