(2R,3R,4S,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol | 669058-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol
• 英文别名: TBDMS(-2)[TBDMS(-3)]Glc(b)-SPh；(2R,3R,4S,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-ol
• CAS: 669058-16-6
• 化学式: C₂₄H₄₄O₅SSi₂
• 分子量: 500.847
• InChiKey: KCKYGPLCWFNGSZ-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2,3-bis-O-tert-butyldimethylsilyl-β-D-glucopyranose 、 2,3-bis-O-tert-butyldimethylsilyl-α-D-glucopyranose
  参考文献：
  名称：

  The first ring inversion of pyranoses induced by bulky silyl protections at the 2- and 3-positions

  摘要：

  The pyranose rings of the 2,3-bis-O-tert-butyldiphenylsilyl-alpha- and beta-D-glucopyranoses, and of the 2,3-bis-O-tert-butyldimethylsilyl-beta-D-glucopyranose were in the C-1(4) form. These findings indicate that the introduction of bulky silyl protecting groups at the 2- and 3-positions can flip a pyranose ring into the axial-rich chair form. Previous such ring inversions have been carried out by the silyl protections at the 3- and 4-positions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.078
• 作为产物：
  描述：

  phenyl 4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 在 2,6-二甲基吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4S,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  The first ring inversion of pyranoses induced by bulky silyl protections at the 2- and 3-positions

  摘要：

  The pyranose rings of the 2,3-bis-O-tert-butyldiphenylsilyl-alpha- and beta-D-glucopyranoses, and of the 2,3-bis-O-tert-butyldimethylsilyl-beta-D-glucopyranose were in the C-1(4) form. These findings indicate that the introduction of bulky silyl protecting groups at the 2- and 3-positions can flip a pyranose ring into the axial-rich chair form. Previous such ring inversions have been carried out by the silyl protections at the 3- and 4-positions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.078

文献信息

• CBr4-photoirradiation protocol for chemoselective deprotection of acid labile primary hydroxyl protecting groups
  作者：Ming-Yi Chen、Laxmikant N. Patkar、Mi-Dan Jan、Adam Shih-Yuan Lee、Chun-Cheng Lin

  DOI：10.1016/j.tetlet.2003.10.205

  日期：2004.1

  CBr4-photoirradiation protocol was found to be a mild, highly efficient and selective method for deprotection of isopropylidene, benzylidene, triphenylmethyl and tert-butyldimethylsilyl protecting groups on sugar molecules. The conditions of this reaction can also be used to cleave peptides off from acid-labile resin linkers in solid-phase peptide synthesis. (C) 2003 Elsevier Ltd. All rights reserved.
• Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions
  作者：Ming-Yi Chen、Laxmikant N. Patkar、Kuo-Cheng Lu、Adam Shih-Yuan Lee、Chun-Cheng Lin

  DOI：10.1016/j.tet.2004.09.095

  日期：2004.12

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.