benzyl N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-2,4-dimethyloxan-3-yl]carbamate | 211804-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-2,4-dimethyloxan-3-yl]carbamate
• CAS: 211804-29-4
• 化学式: C₁₆H₂₃NO₆
• 分子量: 325.362
• InChiKey: JVZRVTOFRFPGKQ-HSMHQDCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-2,4-dimethyloxan-3-yl]carbamate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到methyl callipeltose
  参考文献：
  名称：

  Synthesis of methyl α-l-callipeltoside

  摘要：

  The synthesis of callipeltose, a novel amino sugar with the proposed structure, 4-amino-4,6-dideoxy-2, O-3-C-dimethyl-L-talopyranosyl-3,4-urethane, from L-rhamnose is described. Oxime reduction, carbamate cyclization and selective methylation are key steps. The synthesis supports the assignment of the relative stereochemistry of callipeltose. (C) 1998 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0008-6215(98)00086-x
• 作为产物：
  描述：

  methyl 4-amino-4,6-dideoxy-2,3-O-isopropylidene-3-C-methyl-α-L-talopyranoside 在 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.5h， 生成 benzyl N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-2,4-dimethyloxan-3-yl]carbamate
  参考文献：
  名称：

  Synthesis of methyl α-l-callipeltoside

  摘要：

  The synthesis of callipeltose, a novel amino sugar with the proposed structure, 4-amino-4,6-dideoxy-2, O-3-C-dimethyl-L-talopyranosyl-3,4-urethane, from L-rhamnose is described. Oxime reduction, carbamate cyclization and selective methylation are key steps. The synthesis supports the assignment of the relative stereochemistry of callipeltose. (C) 1998 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0008-6215(98)00086-x

文献信息

• Synthesis of methyl α-l-callipeltoside
  作者：Garry R. Smith、John J. Finley IV、Robert M. Giuliano

  DOI：10.1016/s0008-6215(98)00086-x

  日期：1998.3

  The synthesis of callipeltose, a novel amino sugar with the proposed structure, 4-amino-4,6-dideoxy-2, O-3-C-dimethyl-L-talopyranosyl-3,4-urethane, from L-rhamnose is described. Oxime reduction, carbamate cyclization and selective methylation are key steps. The synthesis supports the assignment of the relative stereochemistry of callipeltose. (C) 1998 Elsevier Science Ltd. Ail rights reserved.