1-dodecyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside | 195006-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-dodecyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside
• 英文别名: (2R,4aR,6R,7R,8S,8aS)-7-amino-6-dodecoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 195006-97-4
• 化学式: C₂₅H₄₁NO₅
• 分子量: 435.604
• InChiKey: FKDFEYBMTCUNMI-KMWHABIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  1-dodecyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 20.0h， 生成 (3aR,4R,6R,7R,7aS)-2-[bis(2-chloroethyl)amino]-4-dodecoxy-6-(hydroxymethyl)-2-oxo-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3,2]oxazaphosphol-7-ol
  参考文献：
  名称：

  糖的烷基化剂。衍生自2-氨基-2-脱氧-d-阿洛糖的环磷酰胺

  摘要：

  摘要通过用相应的2-氨基-2-脱氧-d-阿洛糖衍生物处理相应的2-氨基-2-脱氧-d-阿洛糖衍生物，以良好的收率合成了衍生自烷基2-氨基-4,6-O-亚苄基-2-脱氧-β-d-阿洛吡喃糖苷的环磷酰胺。双（2-氯乙基）磷酰胺二氯化物。成环反应以非常高的非对映选择性发生。随后的氢解得到了衍生自烷基2-氨基-2-脱氧-β-d-allopyranosides的优异的环磷酰胺收率，其亲水性大于前体。起始原料可容易地从2-乙酰氨基-2-脱氧-d-葡萄糖获得。

  DOI：

  10.1016/s0008-6215(98)00056-1
• 作为产物：
  描述：

  十二烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷 在 吡啶 、 氢氧化钾 、 sodium acetate 、 zinc(II) chloride 作用下， 以 乙醇 、 乙二醇甲醚 、 水 为溶剂， 反应 42.0h， 生成 1-dodecyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside
  参考文献：
  名称：

  糖的烷基化剂。衍生自2-氨基-2-脱氧-d-阿洛糖的环磷酰胺

  摘要：

  摘要通过用相应的2-氨基-2-脱氧-d-阿洛糖衍生物处理相应的2-氨基-2-脱氧-d-阿洛糖衍生物，以良好的收率合成了衍生自烷基2-氨基-4,6-O-亚苄基-2-脱氧-β-d-阿洛吡喃糖苷的环磷酰胺。双（2-氯乙基）磷酰胺二氯化物。成环反应以非常高的非对映选择性发生。随后的氢解得到了衍生自烷基2-氨基-2-脱氧-β-d-allopyranosides的优异的环磷酰胺收率，其亲水性大于前体。起始原料可容易地从2-乙酰氨基-2-脱氧-d-葡萄糖获得。

  DOI：

  10.1016/s0008-6215(98)00056-1

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.
• Alkylating agents from sugars. Alkyl hexopyranoside derivatives as carrier systems for chlorambucil
  作者：Fernando Iglesias-Guerra、José I Candela、Juan Bautista、Felipe Alcudia、José M Vega-Pérez

  DOI：10.1016/s0008-6215(99)00030-0

  日期：1999.3

  Chlorambucil derivatives involving alkyl 2-aminodeoxy sugars have been synthesized in good yield by coupling the chlorambucil moiety to positions C-2 or C-3 of the sugar, directly or via a spacer. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose. The final compounds were tested for cytotoxicity, and some of those that presented the best results were studied for inhibition of cell proliferation. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Alkylating agents from sugars. Cyclophosphamides derived from 2-amino-2-deoxy-d-allose
  作者：Fernando Iglesias-Guerra、Isidora Romero、Felipe Alcudia、José M. Vega-Pérez

  DOI：10.1016/s0008-6215(98)00056-1

  日期：1998.3

  Cyclophosphamides derived from alkyl 2-amino-4,6- O -benzylidene-2-deoxy- β - d -allopyranosides have been synthesized with good yield by treatment of the corresponding 2-amino-2-deoxy- d -allose derivatives with bis(2-chloroethyl)phosphoramide dichloride. The ring-forming reaction took place with very high diastereoselectivity. Subsequent hydrogenolysis gave excellent yields of cyclophosphamides derived from alkyl

  摘要通过用相应的2-氨基-2-脱氧-d-阿洛糖衍生物处理相应的2-氨基-2-脱氧-d-阿洛糖衍生物，以良好的收率合成了衍生自烷基2-氨基-4,6-O-亚苄基-2-脱氧-β-d-阿洛吡喃糖苷的环磷酰胺。双（2-氯乙基）磷酰胺二氯化物。成环反应以非常高的非对映选择性发生。随后的氢解得到了衍生自烷基2-氨基-2-脱氧-β-d-allopyranosides的优异的环磷酰胺收率，其亲水性大于前体。起始原料可容易地从2-乙酰氨基-2-脱氧-d-葡萄糖获得。