phenyl 3,4,6-tri-O-acetyl-α-D-gluco-1-thiopyranoside | 143206-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-acetyl-α-D-gluco-1-thiopyranoside
• 英文别名: phenyl 3,4,6-tri-O-acetyl-1-thio-α-D-glucopyranoside；phenylthio 3,4,6-tri-O-acetyl-α-D-glucopyranoside；phenylthio-3,4,6-tri-O-acetyl-α-D-glucopyranoside
• CAS: 143206-82-0
• 化学式: C₁₈H₂₂O₈S
• 分子量: 398.434
• InChiKey: BNPZYPSLAPEUCK-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-α-D-gluco-1-thiopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 硝基甲烷 为溶剂， 反应 5.0h， 生成 methyl 2,6-di-O-benzyl-4,2'-di-O-dimethylsilylene-3-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient stereocontrolled glycosidation of secondary sugar hydroxyls by silicon tethered intramolecular glycosidation

  摘要：

  Dissaccharides containing 1.2-cis glycoside linkages were synthesized by an efficient stereocontrolled two step process involving a silicon tethering step, to a dimethylsilyl acetal followed by intramolecular glycosidation with N-iodosuccinimide in nitromethane.

  DOI：

  10.1016/s0040-4020(01)80200-3
• 作为产物：
  描述：

  potassium thiophenolate 、 3,4,6-tri-O-acetyl-β-D-glucopyranosyl chloride 以63%的产率得到phenyl 3,4,6-tri-O-acetyl-α-D-gluco-1-thiopyranoside
  参考文献：
  名称：

  Stereocontrolled synthesis of α-glucosides by intramolecular glycosidation

  摘要：

  α-葡萄糖苷是通过将苯硫基 3,4,6-三-O-乙酰基-α-D-吡喃葡萄糖苷和醇或酚与二甲基甲硅烷基桥连接，然后进行碘鎓离子催化的分子内糖苷化来制备的。

  DOI：

  10.1039/c39920000913

文献信息

• Application of intramolecular glycosidation to the stereocontrolled synthesis of disaccharides containing α-gluco and α-galacto linkages
  作者：Mikael Bols

  DOI：10.1039/c39930000791

  日期：——

  Disaccharides containing α-glucose and α-galactose linkages are stereospecifically synthesized from primary and secondary sugar hydroxy groups and a 2-hydroxythioglycoside via intramolecular glycosidation of a dimethylsilyl tethered intermediate.

  含有α-葡萄糖和α-半乳糖连接键的二糖通过一种二甲基硅基连接的中间体的分子内糖苷化反应，从初级和次级糖羟基及2-羟基硫糖苷特异性合成。
• Bols, Mikael, Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 829 - 834
  作者：Bols, Mikael

  DOI：——

  日期：——
• Synthesis of Kojitriose using Silicon-Tethered Glycosidation.
  作者：Mikael Bols、Christian Orrenius、Niklas Öhrner、C. Rikard Unelius、Karl Hult、Torbjörn Norin、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0931

  日期：——

  Reaction of 3,4,6-tri-O-acetyl-beta-D-glucopyranosyl chloride (1) with potassium phenylselenate gave phenyl 3,4,6-tri-O-acetyl-1-seleno-alpha,beta-D-glucopyranoside (2) in 59% yield. Silylation of benzyl 3,4,6-tri-O-benzyl-beta-D-glucopyranoside (4) with ethyl 3,4,6-tri-O-benzyl-2-O-chlorodimethylsilyl-1-thio-beta-D-glucopyranoside gave benzyl 2-O-(3,4,6-tri-O-benzyl-1-S-ethyl-1-thio-beta-D-glucopyranos-2-O-yldimethylsilyl)-3,4,6-tri-O-benzyl-beta-D-glucopyranoside (5) in 35% yield. Reaction of 5 with N-iodosuccinimide in nitromethane gave benzyl 2-O-(3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl)-3,4,6-tri-O-benzyl-beta-D-glucopyranoside (6) in 45% yield. Chlorodimethylsilylation of phenyl 3,4,6-tri-O-acetyl-1-seleno-alpha-D-glucopyranoside (2 alpha) and reaction with 6 gave benzyl 2-O-[2-O-(3,4,6-tri-O-acetyl-1-Se-phenyl-1-seleno-alpha-D-glucopyranos-2-O-yldimethylsilyl) -3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl]-3,4,6-tri-O-benzyl-beta-D-glucopyranoside (7) in 82% yield. Intramolecular glycosidation of 7 using N-iodosuccinimide in nitromethane gave benzyl 2-O-[2-O-(3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl)-3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl]-3,4,6-tri-O-benzyl-beta-D-glucopyranoside (8) in 45% yield. Deprotection of 8 gave kojitriose (9) in quantitative yield. Chlorodimethylsilylation of 1,3,4,6-tetra-O-benzyl-alpha,beta-D-fructofuranose (10) with dimethyldichlorosilane and pyridine followed by reaction with ethyl 3,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (3) gave ethyl 2-O-(1,3,4,6-tetra-O-benzyl- alpha,beta-D-fructofuranosyloxydimethylsilyl)-3,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (11) in 85% yield. Chlorodimethylsilylation of 1,3,4,6-tetra-O-benzoyl-alpha-D-fructofuranose (12) with dimethyldichlorosilane and triethylamine followed by reaction with phenyl 3,4,6-tri-O-acetyl-1-thio-alpha-D-glucopyranoside (13) gave phenyl 2-O-(1,3,4,6-tetra-O-benzoyl-alpha-D-fructofuranosyloxydimethylsilyl)-3,4,6-tri-O-acetyl-1-thio-alpha-D-glucopyranoside (14) in 62% yield. Both 11 and 14 failed to undergo intramolecular glycosidation.