methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside | 172603-71-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5S,6R)-5-amino-2,3-dimethoxy-6-methyloxan-4-ol
• CAS: 172603-71-3
• 化学式: C₈H₁₇NO₄
• 分子量: 191.227
• InChiKey: FSRSUTORXUMDGE-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.5h， 生成 methyl 4,6-dideoxy-4-(3-hydroxypropanamido)-2-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Syntheses of the l-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1

  摘要：

  Analogs of the methyl alpha -glycosides of the terminal residues of the O-specific polysaccharides (O-PS) of Vibrio cholerae O:1, serotype Inaba and Ogawa, have been prepared as probes to study their interaction with anti V. cholerae O:1 antibodies. They differ from the termini of the respective O-PSs in anomeric or absolute configuration of perosamine, position of the O-methyl group in D-perosamine, and nature of the N-acyl side chain. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00265-2
• 作为产物：
  描述：

  methyl 4-azido-4,6-dideoxy-3-O-(4-methoxybenzyl)-2-O-methyl-α-D-mannopyranoside 在 吡啶 、 硫化氢 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-l-glycero-tetronamido) - 2-O-methyl-α-d-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa

  摘要：

  Methyl 4-azido-4,6-dideoxy-3-O-benzyl-alpha-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside. Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranose, the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Ogawa. The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group. The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Inaba. The crystal structure of methyl 4,6-dideoxy-2-0-methyl-4-trifluoroacetamido-alpha-D-mannopyranoside is also described.

  DOI：

  10.1016/0008-6215(95)00147-l

文献信息

• Syntheses of fluorinated ligands to probe binding of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, to antibodies
  作者：Alex H.C. Chang、Derek Horton、Pavol Kováč

  DOI：10.1016/s0957-4166(99)00505-4

  日期：2000.2

  Derivatives of methyl alpha-glycosides of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, specifically Fluorinated at position 2' or 4' have been synthesized by coupling the appropriately fluorinated derivatives of 3-deoxy-L-glycero-tetronic acid with the methyl oc-glycosides of perosamine. The compound having the fluorine atom at position 2 was obtained by electrophilic addition of fluorine to the glycal derived from the parent antigenic determinant, serotypes Inaba, using Selectfluor(TM) as a fluorination reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of Some Analogs of the Methyl α-Glycoside of the Presumed Antigenic Determinant of the O-Specific Polysaccharide of<i>Vibrio cholerae</i>O:1, Serotype Ogawa
  作者：Jian Zhang、Pavol Kováč

  DOI：10.1080/07328309808002896

  日期：1998.4

  The following analogs of the title determinant, methyl 4,6-dideoxy-4-(3 -deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, have been prepared: methyl 3,4,6,-trideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(4-hydroxybutyramido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3,4-dideoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3-deoxy-D-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(2-deoxy-L-glycero-tetronamido)2-O-methyl-alpha-D-mannopyranoside, methyl 4-acetamido-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3 -deoxy-L-glycero-tetronamido)-2-O-ethyl-alpha-D-mannopyranoside, and methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-propyl-alpha-D-mannopyranoside.
• Syntheses of the l-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1
  作者：Emmanuel Poirot、Xiaodong Zhang、Noel F. Whittaker、Pavol Kováč

  DOI：10.1016/s0008-6215(00)00265-2

  日期：2001.1

  Analogs of the methyl alpha -glycosides of the terminal residues of the O-specific polysaccharides (O-PS) of Vibrio cholerae O:1, serotype Inaba and Ogawa, have been prepared as probes to study their interaction with anti V. cholerae O:1 antibodies. They differ from the termini of the respective O-PSs in anomeric or absolute configuration of perosamine, position of the O-methyl group in D-perosamine, and nature of the N-acyl side chain. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-l-glycero-tetronamido) - 2-O-methyl-α-d-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa
  作者：Ping-sheng Lei、Yuji Ogawa、Judith L. Flippen-Anderson、Pavol Kováĉ

  DOI：10.1016/0008-6215(95)00147-l

  日期：1995.9

  Methyl 4-azido-4,6-dideoxy-3-O-benzyl-alpha-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside. Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranose, the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Ogawa. The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group. The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Inaba. The crystal structure of methyl 4,6-dideoxy-2-0-methyl-4-trifluoroacetamido-alpha-D-mannopyranoside is also described.