2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: methyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside；methyl 2-O-benzoyl-3,4,6-tetra-O-benzyl-α-D-mannopyranoside；[(2S,3S,4S,5R,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• 化学式: C₃₅H₃₆O₇
• 分子量: 568.667
• InChiKey: YBVGHBZYXAYGKA-MWTNOQARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 硫酸 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 35.0h， 生成 allyl 2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranoside
  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
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-1,2-O-(α-methoxybenzylidene)-β-D-mannopyranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以51%的产率得到2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Unexpected Stereocontrolled Access to 1α,1′β-Disaccharides from Methyl 1,2-Ortho Esters

  摘要：

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1 alpha,1'beta-disaccharides, upon treatment with BF3 center dot Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.

  DOI：

  10.1021/jo202335n

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.
• Unexpected Stereocontrolled Access to 1α,1′β-Disaccharides from Methyl 1,2-Ortho Esters
  作者：Clara Uriel、Juan Ventura、Ana M. Gómez、J. Cristóbal López、Bert Fraser-Reid

  DOI：10.1021/jo202335n

  日期：2012.1.6

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1 alpha,1'beta-disaccharides, upon treatment with BF3 center dot Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.
• Facile synthesis of a comb-like mannohexaose: a trimer of the disaccharide repeating unit of the cell-wall mannans of Aphanoascus mephitatus and related species
  作者：Linsen Heng、Jun Ning、Fanzuo Kong

  DOI：10.1016/s0008-6215(01)00059-3

  日期：2001.4

  An efficient method for the preparation of a comb-like mannohexaose having alpha-(1-->6) and alpha-(1-->2) linkages has been described using 6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-alpha-D-mannopyranosyl trichloroacetimidate as the key glycosyl donor in an 'inverse Schmidt' procedure.

  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。