2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside | 216572-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside
• 英文别名: 2,2',3,3'-tetra-O-benzyl-6,6'-dideoxy-α-D-trehalose；(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-5-hydroxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-2-methyl-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 216572-25-7
• 化学式: C₄₀H₄₆O₉
• 分子量: 670.8
• InChiKey: KXMAJIOZRZARTJ-RSEMBHNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Convenient Divergent Synthesis of a Library of Trehalosamine Analogues

  摘要：

  A library of seven trehalosamine analogues with various natural and non-natural binding motifs was synthesized through an expedient divergent synthetic approach, The final products were prepared in sufficient quantities and purities for different types of assay against various pathogens. Several stereo- and regioselective reactions on the trehalose scaffold were developed for rapid synthesis of all of the designed compounds.

  DOI：

  10.1021/ol026095m
• 作为产物：
  描述：

  2,3,2',3'-tetra-O-benzyl-α,α-trehalose 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Convenient Divergent Synthesis of a Library of Trehalosamine Analogues

  摘要：

  A library of seven trehalosamine analogues with various natural and non-natural binding motifs was synthesized through an expedient divergent synthetic approach, The final products were prepared in sufficient quantities and purities for different types of assay against various pathogens. Several stereo- and regioselective reactions on the trehalose scaffold were developed for rapid synthesis of all of the designed compounds.

  DOI：

  10.1021/ol026095m

文献信息

• Synthesis of trehalose-based compounds and their inhibitory activities against Mycobacterium smegmatis
  作者：Jinhua Wang、Bryan Elchert、Yu Hui、Jon Y. Takemoto、Mekki Bensaci、John Wennergren、Huiwen Chang、Ravi Rai、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2004.09.033

  日期：2004.12

  The synthesis of a library of trehalose-based compounds has been accomplished, and their activities against mycobacterium smegmatis have been determined. A preliminary structure-activity relationship (SAR) is reported. Despite not having a potent lead, one of the trehalose derivatives displays strong activity when applied with isoniazid (INH), which is known to have low sterilizing activity. The bacteriocidal nature of our compounds against Mycobacterium may be significant for the development of new therapies against tuberculosis. (C) 2004 Elsevier Ltd. All rights reserved.
• The Synthesis of Four Dideoxygenated Analogues of β-Maltosyl-(1→4)-Trehalose
  作者：Hans Peter Wessel、Rudolf Minder、Michel Trumtel

  DOI：10.1080/07328309808001900

  日期：1998.11

  Four derivatives of beta-maltosyl-(1 -->4)-trehalose were prepared, each with two deoxy functions in one of the constitutive disaccharide building blocks. 2,3-Di-O-acetyl-4,6-dideoxy-4,6-diiodo-alpha-D-galactopyranosyl-(1-->4) -1,2,3,6-tetra-O-acetyl-D-glucopyranose (3) was employed as a precursor for the 4'",6'" -dideoxygenated tetrasaccharide 9: coupling of 3 with 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3,6-tri-O-benzylidene-alpha-D-glucopyranoside (4) furnished the tetrasaccharide 5 which was deiodinated and deprotected to yield the target tetrasaccharide 9. Secondly, the dideoxygenated maltose derivative 3-deoxy-4,6-O-isopropylidene-2-O-pivaloyl-alpha-D-glucopyranosyl-(1-->4)-1,6- anhydro-3-deoxy-2-O-pivaloyl-beta-D-glucopyranose (10) was ring-opened to the anomeric acetate 11. A [2+2] block synthesis with 4 in TMS triflate mediated glycosylation gave a tetrasaccharide which was deprotected to the 3 ",3'"- dideoxygenated analogue of beta-maltosyl-(1 -->4)-trehalose. For the third tetrasaccharide, 2,3,2',3'-tetra-O-benzyl-alpha,alpha-trehalose was iodinated at the primary positions and deiodinated in the presence of palladium-on-carbon, then this acceptor was selectively glycosylated with hepta-O-acetyl-maltosyl bromide (20). Removal of protective groups furnished the maltosyl trehalose tetrasaccharide deoxygenated at positions C-6 and C-6'. To prepare a 3,3'-dideoxygenated trehalose, the free hydroxyl groups of 2-O-benzyl-4,6-O-(R)-benzylidene-alpha-D-glucopyranosyl 2-O-benzyl-4,6-O-(R)-benzylidene-alpha-D-glucopryanoside (25) were reduced by Barton-McCombie deoxygenation. One of the benzylidene groups was opened reductively with sodium cyanoborohydride. The resulting free hydroxyl group at the 4'-position was glycosylated in a Koenigs-Knorr reaction with 20 to yield the 3,3'-dideoxygenated tetrasaccharide 32, the fourth target oligosaccharide, after deprotection.
• Convenient Divergent Synthesis of a Library of Trehalosamine Analogues
  作者：Yu Hui、Cheng-Wei Tom Chang

  DOI：10.1021/ol026095m

  日期：2002.6.1

  A library of seven trehalosamine analogues with various natural and non-natural binding motifs was synthesized through an expedient divergent synthetic approach, The final products were prepared in sufficient quantities and purities for different types of assay against various pathogens. Several stereo- and regioselective reactions on the trehalose scaffold were developed for rapid synthesis of all of the designed compounds.