(2R,3R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((3S,4R,5R)-3,4,5-tris-benzyloxy-1,1-bis-ethylsulfanyl-hexyl)-tetrahydro-pyran-3-ol | 291282-26-3

• 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: (2R,3R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((3S,4R,5R)-3,4,5-tris-benzyloxy-1,1-bis-ethylsulfanyl-hexyl)-tetrahydro-pyran-3-ol
• 英文别名: (2R,3R,5R,6S)-3-[(3S,4R,5R)-1,1-bis(ethylsulfanyl)-3,4,5-tris(phenylmethoxy)hexyl]-5-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2-methyloxan-3-ol
• CAS: 291282-26-3
• 化学式: C₄₄H₆₆O₇S₂Si
• 分子量: 799.221
• InChiKey: QRCMZJCIKUTUEM-TXNYTWCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.26
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((3S,4R,5R)-3,4,5-tris-benzyloxy-1,1-bis-ethylsulfanyl-hexyl)-tetrahydro-pyran-3-ol 在 palladium on activated charcoal sodium tetrahydroborate 、 甲酸 、 四丁基氟化铵 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 12.5h， 生成 methyl α-D-caryophylloside
  参考文献：
  名称：

  Synthesis of caryophyllose. Use of n-BuLi/Na-O-t-Bu in the coupling of highly functionalized ketones and dithioacetals

  摘要：

  The C-4 branched monosaccharide caryophyllose 2a was synthesized by a convergent approach relying on the coupling of metalated dithioacetal 4b with ketone 3. Combined use of n-BuLi and t-Bu-ONa as deprotonation system for 4b turned out to be decisive for the success off this coupling. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00752-8
• 作为产物：
  描述：

  methyl 2-O-tert-butyldimethylsilyl-3,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose 、 [(2R,3R,4S)-6,6-bis(ethylsulfanyl)-2,4-bis(phenylmethoxy)hexan-3-yl]oxymethylbenzene 在 正丁基锂 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 以47%的产率得到(2R,3R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((3S,4R,5R)-3,4,5-tris-benzyloxy-1,1-bis-ethylsulfanyl-hexyl)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Synthesis of caryophyllose. Use of n-BuLi/Na-O-t-Bu in the coupling of highly functionalized ketones and dithioacetals

  摘要：

  The C-4 branched monosaccharide caryophyllose 2a was synthesized by a convergent approach relying on the coupling of metalated dithioacetal 4b with ketone 3. Combined use of n-BuLi and t-Bu-ONa as deprotonation system for 4b turned out to be decisive for the success off this coupling. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00752-8

文献信息

• Synthesis of caryophyllose. Use of n-BuLi/Na-O-t-Bu in the coupling of highly functionalized ketones and dithioacetals
  作者：Matteo Adinolfi、Gaspare Barone、Pasquale Festa、Luigi Guariniello、Alfonso Iadonisi

  DOI：10.1016/s0040-4039(00)00752-8

  日期：2000.6

  The C-4 branched monosaccharide caryophyllose 2a was synthesized by a convergent approach relying on the coupling of metalated dithioacetal 4b with ketone 3. Combined use of n-BuLi and t-Bu-ONa as deprotonation system for 4b turned out to be decisive for the success off this coupling. (C) 2000 Elsevier Science Ltd. All rights reserved.