benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside | 195006-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside
• 英文别名: benzyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside；(2R,4aR,6R,7R,8S,8aS)-7-amino-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 195006-98-5
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: BOSPELTZTUYCQA-DAUOMPHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 在 乙酸酐 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 6.0h， 生成 2-[(2R,4aR,6R,7R,8S,8aS)-8-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
  参考文献：
  名称：

  Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: application to the synthesis of thiooligosaccharides

  摘要：

  The cyclic sulfamidate of the allosamine derivative 11 is efficiently prepared by reaction with 1,1'-sulfuryl diimidazole; the regioselective opening of this compound by sulfur nucleophiles furnishes 3-thioglucosamine derivatives, useful intermediates in synthesis of thiooligosaccharides.

  DOI：

  10.1039/cc9960000127
• 作为产物：
  描述：

  benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside
  参考文献：
  名称：

  Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: application to the synthesis of thiooligosaccharides

  摘要：

  The cyclic sulfamidate of the allosamine derivative 11 is efficiently prepared by reaction with 1,1'-sulfuryl diimidazole; the regioselective opening of this compound by sulfur nucleophiles furnishes 3-thioglucosamine derivatives, useful intermediates in synthesis of thiooligosaccharides.

  DOI：

  10.1039/cc9960000127

文献信息

• Stereoselective synthesis of oxazolidines from 2-amino-2-deoxy-d-allose derivatives and their reactivity with nucleophiles
  作者：José M. Vega-Pérez、Margarita Vega、Eugenia Blanco、Fernando Iglesias-Guerra

  DOI：10.1016/s0957-4166(00)00498-5

  日期：2001.2

  The use of 2-amino-2-deoxy-D-allose in the synthesis of oxazolidines is described. The reaction takes place with total stereoselectivity in the preparation of both simple oxazolidines (from aldehydes as reagent) and bicyclic oxazolidines (from chlorocarbonyl compounds and keto-acids as reagents). The reactivity of the obtained oxazolidines with hydride and alkylmagnesium chlorides is also described. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of oxiranes using oxazolidines derived from 2-amino-2-deoxy-d-allose as chiral auxiliaries
  作者：José M. Vega-Pérez、Margarita Vega、Eugenia Blanco、Fernando Iglesias-Guerra

  DOI：10.1016/s0957-4166(01)00562-6

  日期：2001.12

  The synthesis of 2,3-epoxyamide derivatives of 2-amino-2-deoxy-D-allose is described. Epoxidation of the corresponding alpha,beta-unsaturated amides with m-CPBA took place with better stereoselectivity when an oxazolidine ring was fused to the 2,3-positions of the sugar molecule. In most cases, both stereoisomers could be isolated and characterized. The stereochemistry of the new stereogenic centers was then determined by cleavage of the,oxirane moiety from the chiral auxiliary, which was also recovered. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: application to the synthesis of thiooligosaccharides
  作者：Begoña Aguilera、Alfonso Fernández-Mayoralas

  DOI：10.1039/cc9960000127

  日期：——

  The cyclic sulfamidate of the allosamine derivative 11 is efficiently prepared by reaction with 1,1'-sulfuryl diimidazole; the regioselective opening of this compound by sulfur nucleophiles furnishes 3-thioglucosamine derivatives, useful intermediates in synthesis of thiooligosaccharides.