2,3,4,6-tetra-O-benzyl-D-glucopyranosyl N-trichloroacetylcarbamate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl N-trichloroacetylcarbamate
• 英文别名: 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranosyl N-trichloroacetylcarbamate；[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] N-(2,2,2-trichloroacetyl)carbamate
• 化学式: C₃₇H₃₆Cl₃NO₈
• 分子量: 729.054
• InChiKey: BNQXYDIDFHEBKQ-BKJHVTENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl N-trichloroacetylcarbamate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以94%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl trichloroacetylcarbamate: a new glycosyl donor for O-glycosylation

  摘要：

  Glycosyl trichloroacetylcarbamates, readily obtained by reacting 1-hydroxy sugars with trichloroacetylisocyanate, have been found as excellent glycosyl donors, and the corresponding O-glycosides are formed in good to excellent yields with a fairly good degree of selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.07.024

文献信息

• Improved catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate: application to various 1-hydroxy sugars
  作者：Tatsuya Shirahata、Jun-ichi Matsuo、Satoko Teruya、Nozomu Hirata、Taku Kurimoto、Nanao Akimoto、Toshiaki Sunazuka、Eisuke Kaji、Satoshi Ōmura

  DOI：10.1016/j.carres.2010.01.011

  日期：2010.4

  Efficient catalytic and stereoselective glycosylation was achieved by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acid in the presence of a glycosyl acceptor and 5A molecular sieves. Catalytic one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was achieved stereoselectively by reaction with trichloroacetyl isocyanate, followed by activation with a catalytic

  在存在糖基受体和5A分子筛的情况下，通过用催化量的路易斯酸活化N-三氯乙酰氨基甲酸糖基，可以实现有效的催化和立体选择性糖基化。通过与三氯乙酰基异氰酸酯反应，然后用催化量的活化剂活化，选择性地实现了1-羟基碳水化合物的催化一锅脱水糖基化反应。
• Synthesis of N-unsubstituted, mono- and disubstituted carbohydrate-1-O-carbamates and their behaviour in glycoside syntheses
  作者：Hans-Peter Knoben、Urs Schlüter、Hartmut Redlich

  DOI：10.1016/j.carres.2004.10.002

  日期：2004.12

  different 1-O-unprotected carbohydrate derivatives (compounds 1-6), representing typical protecting pattern in glycoside synthesis, are described. The carbamate function is N-unsubstituted (compounds 1b-6b), mono- (compounds a: N-trichloroacetyl, c: N-monochloroacetyl, d: N-acetyl, e: N-ethyl, f: N-allyl, g: N-phenyl) or disubstituted (compounds h: imidazolyl, i: N-diethyl, j: N-diphenyl). Additionally

  描述了由六个不同的1-O-未保护的碳水化合物衍生物（化合物1-6）合成的44个1-氨基甲酸酯，它们代表糖苷合成中的典型保护方式。氨基甲酸酯官能团是N-未取代的（化合物1b-6b），单-（化合物a：N-三氯乙酰基，c：N-一氯乙酰基，d：N-乙酰基，e：N-乙基，f：N-烯丙基，g： N-苯基）或二取代的（化合物h：咪唑基，i：N-二乙基，j：N-二苯基）。另外，合成了三种N-氯磺酰基氨基甲酸酯，并用作合成N-未取代的化合物b的中间体。描述并比较了这些化合物的可及性。一些氨基甲酸酯（1、4、5a-j）用作模型化合物，可用于糖苷合成的系统研究。选定的实验数据（反应条件，端基异构体比例，旋转值，
• Catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate
  作者：Jun-ichi Matsuo、Tatsuya Shirahata、Satoshi Ōmura

  DOI：10.1016/j.tetlet.2005.11.027

  日期：2006.1

  Catalytic and stereoselective glycosylation efficiently proceeded by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acids in the presence of a glycosyl acceptor and molecular sieves 5 angstrom. Catalytic and one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was also performed stereoselectively by the reaction with trichloroacetyl isocyanate followed by activation with a catalytic amount of activators. (c) 2005 Elsevier Ltd. All rights reserved.
• Sequential one-pot glycosylation with glycosyl N-trichloroacetylcarbamate and trichloroacetate including dehydrative approach using 1-hydroxy sugars
  作者：Tatsuya Shirahata、Asami Kojima、Satoko Teruya、Jun-ichi Matsuo、Masaki Yokoyama、Shogo Unagiike、Toshiaki Sunazuka、Kazuishi Makino、Eisuke Kaji、Satoshi Ōmura、Yoshinori Kobayashi

  DOI：10.1016/j.tet.2011.06.006

  日期：2011.9

  An efficient sequential one-pot glycosylation has been developed with glycosyl trichlorocarbamate and trichloroacetate activated by the same Lewis acid and enabled by a change in reaction temperature. The act-selective glycosylation was achieved using glucose, galactose, and mannose substrates after investigation into the reactivities of the two types of glycosyl donors. Sequential one-pot dehydrative glycosylation, including in situ preparation of glycosyl donors followed by generation of two glycosyl bonds, provided three types of trisaccharide. (C) 2011 Published by Elsevier Ltd.