benzyl 2,3,4,6-tetra-O-acetyl-1-sulfonyl-α-D-mannopyranoside | 1048006-19-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl 2,3,4,6-tetra-O-acetyl-1-sulfonyl-α-D-mannopyranoside
• 英文别名: benzyl 2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl sulfone；[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-benzylsulfonyloxan-2-yl]methyl acetate
• CAS: 1048006-19-4
• 化学式: C₂₁H₂₆O₁₁S
• 分子量: 486.497
• InChiKey: MRZSJUJERZJQOD-CRSSMBPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4,6-tetra-O-acetyl-1-sulfonyl-α-D-mannopyranoside 在 甲醇 、 potassium carbonate 作用下， 以87%的产率得到benzyl α-d-mannopyranosyl sulfone
  参考文献：
  名称：

  α-d-Mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II

  摘要：

  Human Golgi alpha-mannosidase II (hGM) is a pharmaceutical target for the design of inhibitors with antitumor activity. Nanomolar inhibitors of hGM exhibit unwanted co-inhibition of the human lysosomal alpha-mannosidase (hLM). Hence, improving specificity of the inhibitors directed toward hGM is desired in order to use them in cancer chemotherapy. We report on the rapid synthesis of D-mannose derivatives having one of the RS-. R(SO)- or R(SO(2))- groups at the alpha-anomeric position. Inhibitory properties of thirteen synthesized alpha-D-mannopyranosides were tested against the recombinant enzyme Drosophila melanogaster homolog of hGM (dGMIIb) and hLM (dLM408). Derivatives with the sulfonyl [R(SO(2))-] group exhibited inhibitory activities at the mM level toward both dGMIIb (IC(50) = 1.5-2.5 mM) and dLM408 (IC(50) = 1.0-2.0 mM). Among synthesized, only the benzylsulfonyl derivative showed selectivity toward dGMIIb. Its inhibitory activity was explained based on structural analysis of the built 3-D complexes of the enzyme with the docked compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.012
• 作为产物：
  描述：

  4,6-di-O-acetyl-D-glucal 在 吡啶 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 1,1'-双(二苯基膦)二茂铁 、 sodium periodate 、 bis(benzonitrile)palladium(II) chloride 、 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.5h， 生成 benzyl 2,3,4,6-tetra-O-acetyl-1-sulfonyl-α-D-mannopyranoside
  参考文献：
  名称：

  Pd催化烯丙基重排非对映选择性合成硫苷

  摘要：

  立体选择性糖基化在碳水化合物化学中具有挑战性。在此，通过钯催化的烯丙基重排对糖醛进行立体选择性硫代糖基化，可在 α-异构体硫糖苷上产生各种取代基。通过硫代硫酸盐与衍生自葡萄糖、阿拉伯糖、半乳糖和鼠李糖的糖苷的组合，获得了两个综合系列的芳基和苄基硫糖苷。此外，薯蓣基 α-l-鼠李糖苷和异槲皮苷分别通过 α-亚砜-鼠李糖苷和 α-亚砜-葡萄糖苷的立体特异性 [2,3]-σ 重排实现了选择性。

  DOI：

  10.1021/acs.orglett.1c03302

文献信息

• Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)–C(3) Unsaturated and α-<scp>d</scp>-Mannopyranosyl Sulfones
  作者：Sravanthi Chittela、Thurpu Raghavender Reddy、Palakodety Radha Krishna、Sudhir Kashyap

  DOI：10.1021/acs.joc.5b00975

  日期：2015.7.17

  An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and a-p-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access alpha-n-mannopyranosyl sulfones in good yields with high regioselectivity.
• Application of HOF·CH3CN to the synthesis of glycosyl sulfones
  作者：Goreti Ribeiro Morais、Andrew J. Humphrey、Robert A. Falconer

  DOI：10.1016/j.tet.2008.05.033

  日期：2008.7

  A fast, complete and clean conversion of thioglycosides into glycosyl sull'ones under mild acidic conditions is described, using the HOF center dot CH3CN complex at room temperature. This methodology affords glycosyl sull'ones in high yields and in excellent purity. (c) 2008 Elsevier Ltd. All rights reserved,