methyl 2-N-benzylamino-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside | 330825-80-4

• 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)-α-D-ribo-hexopyranoside
• CAS: 330825-80-4
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: BBINBDHRWVEBHP-XNTOXWQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-N-benzylamino-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside 在 palladium dihydroxide 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 26.0h， 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：

  methyl 2-(N-benzylamino)-2,3-dideoxy-4,6-O-phenylmethylene-3C-phenylsulfonyl-α-D-glucopyranoside 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以90%的产率得到methyl 2-N-benzylamino-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

文献信息

• Ravindran; Pathak, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2001, vol. 40, # 11, p. 1114 - 1120
  作者：Ravindran、Pathak

  DOI：——

  日期：——