phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-glucopyranoside | 861927-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-2-phenylsulfanyl-6-(trityloxymethyl)oxane
• CAS: 861927-81-3
• 化学式: C₅₂H₄₈O₅S
• 分子量: 785.016
• InChiKey: IILPYWOFUQYONX-PKVCVKGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  58
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-glucopyranoside 在 水 、 溶剂黄146 作用下， 以95%的产率得到phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  从萌发的水芹种子的粘液中合成高效的化感物质鳞翅类化合物的合成和绝对构型

  摘要：

  由D-葡萄糖和α-L-鼠李糖合成了1，2-顺式联结的双糖莱皮莫胺（1），用于确定绝对构型。

  DOI：

  10.1016/s0040-4039(00)77648-9
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 吡啶 、 甲醇 、 sodium methylate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-glucopyranoside
  参考文献：
  名称：

  从萌发的水芹种子的粘液中合成高效的化感物质鳞翅类化合物的合成和绝对构型

  摘要：

  由D-葡萄糖和α-L-鼠李糖合成了1，2-顺式联结的双糖莱皮莫胺（1），用于确定绝对构型。

  DOI：

  10.1016/s0040-4039(00)77648-9

文献信息

• Selective deprotection of terminal isopropylidene acetals and trityl ethers using HClO4 supported on silica gel
  作者：Aditi Agarwal、Yashwant D. Vankar

  DOI：10.1016/j.carres.2005.04.005

  日期：2005.7

  Terminal isopropylidene acetals are selectively cleaved to the corresponding 1,2-diols in good to excellent yields in 6-24 h at room temperature by using the 'HClO4.SiO2' reagent system. Likewise, trityl ethers are readily cleaved to the corresponding alcohols in good to excellent yields within 2-3 h at room temperature. Work-up involves merely filtration of the reagent followed by purification of

  通过使用'HClO4.SiO2'试剂系统，在室温下于6-24小时内将末端异亚丙基缩醛以良好至极好的收率选择性裂解为相应的1,2-二醇。同样，在室温下2-3小时内，三苯甲基醚很容易以良好或优异的收率裂解成相应的醇。后处理仅涉及试剂的过滤，然后纯化粗产物。
• Synthesis and absolute configuration of lepidimoide, a high potent allelopathic substance from mucilage of germinated cress seeds
  作者：Seiji Kosemura、Shosuke Yamamura、Hideo Kakuta、Junya Mizutani、Koji Hasegawa

  DOI：10.1016/s0040-4039(00)77648-9

  日期：1993.4

  Lepidimoide (1), 1,2-cis-linked disaccharide, was synthesized from D-glucose and α-L-rhamnose for determination of the absolute configuration.

  由D-葡萄糖和α-L-鼠李糖合成了1，2-顺式联结的双糖莱皮莫胺（1），用于确定绝对构型。
• Stereodirecting Effect of the Pyranosyl C-5 Substituent in Glycosylation Reactions
  作者：Jasper Dinkelaar、Ana Rae de Jong、Robert van Meer、Mark Somers、Gerrit Lodder、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo900662v

  日期：2009.7.17

  The stereodirecting effect of the glycosyl C-5 substituent has been investigated in a series of D-pyranosyl thioglycoside donors and related to their preferred positions in the intermediate H-3(4) and H-4(3) half-chair oxacarbenium ions. Computational studies showed that an axially positioned C-5 carboxylate ester can stabilize the (3)H4 half-chair oxacarbenium ion conformer by donating electron densit from its carbonyl function into the electron-poor oxacarbenium ion functionality. A similar stabilization can be achieved by a C-5 benzyloxyrnethyl group, but,the magnitude of this stabilization is significantly smaller than for the C-5 carboxylate ester. As a result, the preference of the C-5 benzyloxymethyl to occupy an axial position in the half-chair oxacarbenium ions is much reduced compared to the C-5 carboxylate ester. To minimize steric interactions, a C-5 methyl group prefers to adopt an equatorial position and therefore favors the H-4(3) half-chair oxacarbenium ion. When all pyranosyl substituents occupy their favored position in one of the two intermediate half-chair oxacarbenium ions, highly stereoselective glycosylations can be achieved as revealed by the excellent beta-selectivity of mannuronate esters and alpha-selectivity of 6-deoxygulosides.