4-oxobutyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 331686-13-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-oxobutyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: 4-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybutanal
• CAS: 331686-13-6
• 化学式: C₃₈H₄₂O₇
• 分子量: 610.747
• InChiKey: HUMZOURMEAWUSX-HRTJLHCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 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：

  4-oxobutyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal ammonium formate 、 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 30.0h， 生成 2-(N-(4-(α-D-glucopyranosyloxy)butyl)amino)benzamide
  参考文献：
  名称：

  Fluorescence labelling of carbohydrates with 2-aminobenzamide (2AB)

  摘要：

  2-Aminobenzamide (2AB) is a common fluorescence label attached to reducing oligosaccharides by a reductive amination procedure. Chemical investigation of the published literature procedure reveals labelling occurs by the expected mechanism for both protected and unprotected glucose derivatives to yield open-chain carbohydrates rather than result in the formation of any heterocyclic materials. Pentenyl glucosides may also be readily attached to the 2AB label by a sequence of dihydroxylation, periodate cleavage and subsequent reductive amination of the resulting aldehyde. :,AB labelling is compatible with deprotection of both acetate and benzyl protecting groups. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00477-8
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran 在 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 为溶剂， 反应 33.0h， 生成 4-oxobutyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Fluorescence labelling of carbohydrates with 2-aminobenzamide (2AB)

  摘要：

  2-Aminobenzamide (2AB) is a common fluorescence label attached to reducing oligosaccharides by a reductive amination procedure. Chemical investigation of the published literature procedure reveals labelling occurs by the expected mechanism for both protected and unprotected glucose derivatives to yield open-chain carbohydrates rather than result in the formation of any heterocyclic materials. Pentenyl glucosides may also be readily attached to the 2AB label by a sequence of dihydroxylation, periodate cleavage and subsequent reductive amination of the resulting aldehyde. :,AB labelling is compatible with deprotection of both acetate and benzyl protecting groups. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00477-8

文献信息

• Fluorescence labelling of carbohydrates with 2-aminobenzamide (2AB)
  作者：Robert R. France、Ian Cumpstey、Terry D. Butters、Antony J. Fairbanks、Mark R. Wormald

  DOI：10.1016/s0957-4166(00)00477-8

  日期：2000.12

  2-Aminobenzamide (2AB) is a common fluorescence label attached to reducing oligosaccharides by a reductive amination procedure. Chemical investigation of the published literature procedure reveals labelling occurs by the expected mechanism for both protected and unprotected glucose derivatives to yield open-chain carbohydrates rather than result in the formation of any heterocyclic materials. Pentenyl glucosides may also be readily attached to the 2AB label by a sequence of dihydroxylation, periodate cleavage and subsequent reductive amination of the resulting aldehyde. :,AB labelling is compatible with deprotection of both acetate and benzyl protecting groups. (C) 2001 Elsevier Science Ltd. All rights reserved.