2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate | 565462-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]5-thio-Glc(a)-O-C(NH)CCl3；[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)thian-2-yl] 2,2,2-trichloroethanimidate
• CAS: 565462-71-7
• 化学式: C₃₆H₃₆Cl₃NO₅S
• 分子量: 701.111
• InChiKey: GKWNCZLTWWPSIZ-RUOAZZEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranose 、 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate 在 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到1,2,3,4-tetra-O-benzoyl-6-O-[2',3',4',6'-tetra-O-benzyl-5'-deoxy-5'-thio-α-D-glucopyranosyl]-5-deoxy-5-thio-α-D-glucopyranose
  参考文献：
  名称：

  α-Selective glycosylation with 5-thioglucopyranosyl donors; synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units

  摘要：

  A general method for alpha-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00072-6
• 作为产物：
  描述：

  tetrahydropyran-2-yl 5-deoxy-5-thio-α-D-glucopyranoside 在 高氯酸 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units

  摘要：

  Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent P-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.028

文献信息

• α-Selective glycosylation with 5-thioglucopyranosyl donors; synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units
  作者：Hiroko Matsuda、Keiichiro Ohara、Yasuharu Morii、Masaru Hashimoto、Kazuo Miyairi、Toshikatsu Okuno

  DOI：10.1016/s0960-894x(03)00072-6

  日期：2003.3

  A general method for alpha-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units
  作者：Yasuharu Morii、Hiroko Matsuda、Keiichiro Ohara、Masaru Hashimoto、Kazuo Miyairi、Toshikatsu Okuno

  DOI：10.1016/j.bmc.2005.05.028

  日期：2005.9

  Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent P-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. (c) 2005 Elsevier Ltd. All rights reserved.