6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl trichloroacetimidate | 220903-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bn(-3)][Bn(-4)]Man6Ac(a)-O-C(NH)CCl3；[(2R,3S,4S,5R,6R)-6-(acetyloxymethyl)-4,5-bis(phenylmethoxy)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 220903-22-0
• 化学式: C₃₁H₃₀Cl₃NO₈
• 分子量: 650.94
• InChiKey: YKEGYQVNUGSDQV-DMYSPCIHSA-N

物化性质

• 沸点：
  660.5±65.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 octyl 3,4-di-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthetic disaccharide analogs as potential substrates and inhibitors of a mycobacterial polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase

  摘要：

  Analogs of the alpha-D-Manp-(1 --> 6)-alpha-D-Manp-O(CH2)(7)CH3 disaccharide 4, a known substrate for a polyprenol monophosphomannose-dependent alpha-(1-->6)-mannosyltransferase involved in mycobacterial LAM biosynthesis, have been synthesized and screened as potential substrates and inhibitors of the enzyme. In the disaccharides synthesized, the hydroxyl groups at C-2 and C-6 on the reducing end residue have been replaced by combinations of amino, fluoro, and methoxy functionalities 9-14. In addition, a disaccharide in which the nonreducing mannopyranose residue was replaced with a 3,6-anhydromannopyranose residue 34 was synthesized from a byproduct formed during one of the reactions leading to 14. When tested against the enzyme, none were active as substrates, as would be expected as all lack the C-6' hydroxyl group to which, an additional sugar residue would be transferred. Evaluation of these compounds as inhibitors of the enzyme revealed that only three, 11, 12, and 13, all of which contain one or more amino groups, inhibited the enzyme. The most potent inhibitor was the diamino-disaccharide, 11. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.063
• 作为产物：
  描述：

  1,6-di-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranose 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  易于合成梳状甘露糖：Aphanoascus mephitatus和相关物种的细胞壁甘露聚糖的二糖重复单元的三聚体。

  摘要：

  已经描述了使用6-O-乙酰基-2-O-苯甲酰基-3制备具有α-（1-> 6）和α-（1-> 2）键的梳状甘露糖的有效方法在“ Schmidt逆过程”中，关键的糖基供体是4,4-二-O-苄基-α-D-甘露吡喃糖基三氯乙酰亚氨酸。

  DOI：

  10.1016/s0008-6215(01)00059-3

文献信息

• Facile syntheses of a hexasaccharide and a nonasaccharide related to the cell wall D-mannan of yeast Candida albicans
  作者：Jun Ning、Fanzuo Kong

  DOI：10.1016/s0040-4039(98)02625-2

  日期：1999.2

  A highly efficient strategy for the preparation of D-manno-hexa- and nonasaccharides related to the cell wall D-mannan of yeast Candida albicans having alpha-(1-->6)- and alpha-(1-->2)-linkages has been developed using 6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-alpha-D-mannopyranosyl trichloroacetimidate (7) as the key glycosyl donor in the "Inverse Schmidt" procedure. (C) 1999 Elsevier Science Ltd. All rights reserved.