methyl 7-amino-6,7-dideoxy-α-D-manno-heptopyranoside | 263328-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 7-amino-6,7-dideoxy-α-D-manno-heptopyranoside
• 英文别名: (2R,3S,4S,5S,6S)-2-(2-aminoethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 263328-53-6
• 化学式: C₈H₁₇NO₅
• 分子量: 207.227
• InChiKey: XSPPKTXLFZRDBZ-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 7-amino-6,7-dideoxy-α-D-manno-heptopyranoside 在 calcium carbonate 作用下， 以 吡啶 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 methyl 2,3,4-tri-O-acetyl-6,7-dideoxy-7-isothiocyanato-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates

  摘要：

  Methyl 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco (manno)(galacto)-heptopyranosides have been synthesized in four steps by homologation of the respective methyl hexopyranosides via the corresponding heptopyranosydurononitriles. Neither intra- nor intermolecular thiocarbamate formation was observed, even under rather strenuous acidic or basic conditions. The reducing derivative 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco-heptopyranose was also a stable compound in aqueous solution in the absence of base. Formation of a six-membered intramolecular cyclic thiocarbamate was achieved in DMF solution in the presence of triethylamine. The title compounds are the first examples of stable fully unprotected monosaccharide isothiocyanates.

  DOI：

  10.1016/s0008-6215(99)00273-6
• 作为产物：
  描述：

  methyl 6-deoxy-6-iodo-α-D-mannopyranoside 在 diborane-dimethylsulfide complex 作用下， 以 吡啶 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 methyl 7-amino-6,7-dideoxy-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates

  摘要：

  Methyl 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco (manno)(galacto)-heptopyranosides have been synthesized in four steps by homologation of the respective methyl hexopyranosides via the corresponding heptopyranosydurononitriles. Neither intra- nor intermolecular thiocarbamate formation was observed, even under rather strenuous acidic or basic conditions. The reducing derivative 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco-heptopyranose was also a stable compound in aqueous solution in the absence of base. Formation of a six-membered intramolecular cyclic thiocarbamate was achieved in DMF solution in the presence of triethylamine. The title compounds are the first examples of stable fully unprotected monosaccharide isothiocyanates.

  DOI：

  10.1016/s0008-6215(99)00273-6

文献信息

• Synthesis of Mannose-6-Phosphate Analogues and their Utility as Angiogenesis Regulators
  作者：Véronique Barragan-Montero、Azzam Awwad、Stéphanie Combemale、Pascal de Santa Barbara、Bernard Jover、Jean-Pierre Molès、Jean-Louis Montero

  DOI：10.1002/cmdc.201100293

  日期：2011.10.4

  Sweet utility: An efficient approach, using a key cyclic sulfate intermediate is reported for the synthesis of mannose‐6‐phosphate (M6P) analogues modified at the C‐6 position. These analogues represent the first known monosaccharide effectors of angiogenesis; furthermore, the results reported here confirm the involvement of the M6P receptor in blood vessel formation.

  实用价值低：据报道，一种有效的方法使用关键的环状硫酸盐中间体合成了在C-6位置修饰的甘露糖-6-磷酸酯（M6P）类似物。这些类似物代表了第一个已知的血管生成单糖效应子。此外，此处报道的结果证实了M6P受体参与了血管形成。
• NOVEL USES OF D-MANNOPYRANOSE DERIVATIVES ACTIVATING ANGIOGENESIS
  申请人：Montero Jean-Louis

  公开号：US20110124558A1

  公开（公告）日：2011-05-26

  The invention relates to the use of certain derivatives of D-mannopyranoside for controlling angiogenesis. These compounds have a pro-angiogenic activity, and can particularly be used for preparing a pharmaceutical composition for treating cardiovascular diseases or for treating muscular atrophy. The invention also relates to certain D-mannopyranoside derivatives, to a pharmaceutical or cosmetic composition containing said derivatives, and to the use of such a cosmetic composition for preventing and/or treating hair loss.

  该发明涉及利用某些D-甘露聚糖衍生物来控制血管生成。这些化合物具有促血管生成活性，特别适用于制备用于治疗心血管疾病或肌肉萎缩的药物组合物。该发明还涉及某些D-甘露聚糖衍生物，含有该衍生物的药用或化妆品组合物，以及利用此类化妆品组合物预防和/或治疗脱发。
• US8551960B2
  申请人：——

  公开号：US8551960B2

  公开（公告）日：2013-10-08
• Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates
  作者：Juan Manuel Benito、Carmen Ortiz Mellet、José Manuel Garcı́a Fernández

  DOI：10.1016/s0008-6215(99)00273-6

  日期：1999.1

  Methyl 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco (manno)(galacto)-heptopyranosides have been synthesized in four steps by homologation of the respective methyl hexopyranosides via the corresponding heptopyranosydurononitriles. Neither intra- nor intermolecular thiocarbamate formation was observed, even under rather strenuous acidic or basic conditions. The reducing derivative 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco-heptopyranose was also a stable compound in aqueous solution in the absence of base. Formation of a six-membered intramolecular cyclic thiocarbamate was achieved in DMF solution in the presence of triethylamine. The title compounds are the first examples of stable fully unprotected monosaccharide isothiocyanates.