methyl 2-(N-benzylamino)-2,3-dideoxy-4,6-O-phenylmethylene-3C-phenylsulfonyl-α-D-glucopyranoside | 293294-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(N-benzylamino)-2,3-dideoxy-4,6-O-phenylmethylene-3C-phenylsulfonyl-α-D-glucopyranoside
• 英文别名: Methyl 2-N-Benzylamino-2,3-dideoxy-4,6-O-(phenyl methylene)-3-C-phenylsulfonyl a\-D-glucopyranoside；(2R,4aR,6S,7S,8R,8aR)-8-(benzenesulfonyl)-N-benzyl-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-amine
• CAS: 293294-12-9
• 化学式: C₂₇H₂₉NO₆S
• 分子量: 495.596
• InChiKey: KFZSLTUWCJHHRX-XXVOEFFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(N-benzylamino)-2,3-dideoxy-4,6-O-phenylmethylene-3C-phenylsulfonyl-α-D-glucopyranoside 在 palladium dihydroxide 吡啶 、 氢气 、 magnesium 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 37.0h， 生成 methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Vinylsulfone-modified carbohydrates: first general route to d-lividosamine (2-amino-2,3-dideoxy-d-glucose) and its new analogues

  摘要：

  A general route to D-lividosamine and its new analogues has been devised for the first time. The essence of the present synthetic route lies in the diastereoselective introduction of N-monoalkylated and N-dialkylated amines to C-2 carbons of methyl 2,3-dideoxy-3-C-phenylsulfonyl-alpha -D-hex-2-enopyranoside and methyl 2,3-dideoxy-3-C-phenylsulfonyl-P-D-hex-2-enopyranoside in equatorial configurations. The 2-amino-2,3-didcoxysugrs thus generated, are desulfonated reductively at C-3 sites to produce a known intermediate for the synthesis of D-lividosamine and several new 2-N-alkylamino- acid 2-N,N-dialkylamino-2,3-dideoxy analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01081-4
• 作为产物：
  描述：

  苄胺 、 methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-C-phenylsulfonyl-α-D-erythro-hex-2-enopyranoside 生成 methyl 2-(N-benzylamino)-2,3-dideoxy-4,6-O-phenylmethylene-3C-phenylsulfonyl-α-D-glucopyranoside
  参考文献：
  名称：

  Comparison of the two anomers of methyl 2-(N-benzylamino)-2,3-dideoxy-4,6-O-phenylmethylene-3-C-phenylsulfonyl-D-glucopyranoside

  摘要：

  The title compounds, the alpha and beta anomers of methyl 2-(N-benzylamino)-2,3-dideoxy-4,6-O-phenylmethylene-3-C- phenylsulfonyl-D-glucopyranoside, C27H29NO6S, belong to the class of deoxyamino-sugars prepared by the addition of amines at C2. The endocyclic bond lengths of the pyranose ring in the alpha anomer are shorter than the corresponding bonds in the alpha anomer. The pyranose ring is in the chair form in the former, while it is in the boat form in the latter. These observed differences could be attributed to the C2 substitution of a bulky group. The phenylsulfonyl and benzylamino groups are in equatorial positions in the alpha anomer, while the benzylamino group is axial in the beta anomer.

  DOI：

  10.1107/s0108270100007344