2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate | 565462-72-8

• 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-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2,3,4,6-O-tetrakis(4-methoxyphenylmethyl)-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate；Mob(-2)[Mob(-3)][Mob(-4)][Mob(-6)]5-thio-Glc(a)-O-C(NH)CCl3；[(2S,3R,4S,5S,6R)-3,4,5-tris[(4-methoxyphenyl)methoxy]-6-[(4-methoxyphenyl)methoxymethyl]thian-2-yl] 2,2,2-trichloroethanimidate
• CAS: 565462-72-8
• 化学式: C₄₀H₄₄Cl₃NO₉S
• 分子量: 821.216
• InChiKey: IMRFVFVRDOWFDX-HRTJLHCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate 在 甲醇 、 三乙基硅基三氟甲磺酸酯 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 methyl 6-O-(5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside
  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 盐酸 、 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 、 甲苯 、 苯 为溶剂， 反应 2.0h， 生成 2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-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

• Synthesis of thiosaccharides employing the Pummerer rearrangement of tetrahydrothiopyran oxides
  作者：Junji Fujita、Hiroko Matsuda、Kazunori Yamamoto、Yasuharu Morii、Masaru Hashimoto、Toshikatsu Okuno、Kimiko Hashimoto

  DOI：10.1016/j.tet.2004.06.006

  日期：2004.8

  The Pummerer rearrangement of 1-deoxy-5-thioglucopyranose derivatives carrying acetonides at the C3,4-positions proceeded regioselectively at the C1 position by treating with TFAA in the presence of pyridine. Studies employing deuterium-labelled derivatives revealed that the reaction was induced by E2 1,2-elimination of trifluoroacetic acid of the trifluoroacetoxy sulfonium intermediate. This methodology

  通过在吡啶存在下用TFAA处理，在C1,4-位带有丙酮化物的1-脱氧-5-硫代吡喃葡萄糖衍生物的Pummerer重排在C1位置区域选择性地进行。使用氘标记衍生物的研究表明，该反应是通过E2 1,2-消除三氟乙酰氧基sulf中间体的三氟乙酸诱导的。该方法学应用于由5-硫代吡喃葡萄糖苷单元组成的异麦芽三糖衍生物的合成。