N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serine methyl ester | 1038587-86-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serine methyl ester
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2S)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propoxy]oxan-2-yl]methyl benzoate
• CAS: 1038587-86-8
• 化学式: C₄₆H₄₁NO₁₄
• 分子量: 831.83
• InChiKey: CWJDDGIBZIJNKT-DTZSTUMFSA-N

物化性质

• 沸点：
  919.3±65.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  188
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  perbenzoyl-D-glucopyranosyl o-(1-hexynyl)benzoate 、 N-苄氧羰酰基-L-丝氨酸甲酯 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以71%的产率得到N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serine methyl ester
  参考文献：
  名称：

  Homogeneous Gold-Catalyzed Glycosylations in Continuous Flow

  摘要：

  The use of versatile alkynyl-building blocks that are activated by gold(I)-catalysis is demonstrated to efficiently generate a variety of glycosides in continuous flow. The application of a continuous flow setting to gold(I)-catalyzed glycosylations enables very short reaction times and excellent control of the reaction conditions.

  DOI：

  10.1021/acs.orglett.5b01584

文献信息

• Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters
  作者：Teiichi Murakami、Yukari Sato、Motonari Shibakami

  DOI：10.1016/j.carres.2008.03.019

  日期：2008.6

  Reactions of O-benzoylated glucopyranosyl halide (I, Br), isolated or generated in situ from per-benzoylated glucose (8a) and trimethylsilyl halide, with various alcohols were efficiently promoted by zinc halide (Cl, Br) or N-bromosuccinimide with a catalytic ZnI2 to give the corresponding 1,2- trans-beta-glucosides in good to high yields. When the anomeric halogenation of 8a was carried out in the presence of reactive alcohols, 1,2-cis-alpha-glucosides were selectively formed. (C) 2008 Elsevier Ltd. All rights reserved.
• Homogeneous Gold-Catalyzed Glycosylations in Continuous Flow
  作者：Stefan Matthies、D. Tyler McQuade、Peter H. Seeberger

  DOI：10.1021/acs.orglett.5b01584

  日期：2015.8.7

  The use of versatile alkynyl-building blocks that are activated by gold(I)-catalysis is demonstrated to efficiently generate a variety of glycosides in continuous flow. The application of a continuous flow setting to gold(I)-catalyzed glycosylations enables very short reaction times and excellent control of the reaction conditions.