2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranosyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranoside | 129729-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranosyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(trifluoromethylsulfonyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl trifluoromethanesulfonate
• CAS: 129729-12-0
• 化学式: C₅₆H₅₆F₆O₁₅S₂
• 分子量: 1147.17
• InChiKey: RRNDVSUNFFVBAA-IPCGEZBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  79
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  187
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranosyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranoside 在 palladium dihydroxide sodium hydroxide 、 sodium azide 、 氢气 、 三乙胺 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 6,6'-didecanamido-6,6'-dideoxy-α,α-D-trehalose
  参考文献：
  名称：

  Synthesis of trehalose-based compounds and their inhibitory activities against Mycobacterium smegmatis

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.09.033
• 作为产物：
  描述：

  三氟甲磺酸酐 、 [(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranosyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranoside
  参考文献：
  名称：

  新的α，α-海藻糖杂环衍生物的合成

  摘要：

  摘要从商业上制备了具有潜在合成和药理学意义的几种新颖的N-1，N-2和S -5四唑以及在C-6,6'处被二取代的α，α-海藻糖的1,3,4-恶二唑衍生物。四唑和1,3,4-恶二唑与六-O-苄基-6,6'-二-O-triflyl-α，α-海藻糖反应。

  DOI：

  10.1016/j.carres.2007.11.019

文献信息

• Synthesis of New Disugar Phosphine Ligands and Their Use in Asymmetric Hydrogenation
  作者：Scott R. Gilbertson、Cheng-Wei T. Chang

  DOI：10.1021/jo00124a051

  日期：1995.9
• BAER, HANS H.;BRETON, ROGER L.;SHEN, YAPING, CARBOHYDR. RES., 200,(1990) C. 377-389
  作者：BAER, HANS H.、BRETON, ROGER L.、SHEN, YAPING

  DOI：——

  日期：——
• 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.
• Synthesis of new heterocyclic derivatives of α,α-trehalose
  作者：Inácio Luduvico、Mara R.C. Couri、Leandro J. dos Santos、Maria A.F. Prado、Rossimiriam P. Freitas Gil、Rosemeire B. Alves

  DOI：10.1016/j.carres.2007.11.019

  日期：2008.2

  Abstract Several novel N-1, N-2, and S -5 tetrazole and 1,3,4-oxadiazole derivatives of α,α-trehalose disubstituted at C-6,6′, with potential synthetic and pharmacological interest were prepared from commercial tetrazoles and 1,3,4-oxadiazoles in reaction with hexa- O -benzyl-6,6′-di- O -triflyl-α,α-trehalose.

  摘要从商业上制备了具有潜在合成和药理学意义的几种新颖的N-1，N-2和S -5四唑以及在C-6,6'处被二取代的α，α-海藻糖的1,3,4-恶二唑衍生物。四唑和1,3,4-恶二唑与六-O-苄基-6,6'-二-O-triflyl-α，α-海藻糖反应。