Dibenzyl-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yl)-amine | 220911-61-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Dibenzyl-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yl)-amine
• 英文别名: (2S,3R,4R,5R,6R)-N,N-dibenzyl-2-methylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-amine
• CAS: 220911-61-5
• 化学式: C₄₂H₄₅NO₄S
• 分子量: 659.89
• InChiKey: FQKGATQPUOXRNY-DJLQKWJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dibenzyl-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yl)-amine 在 palladium dihydroxide 盐酸 、 4 A molecular sieve 、 dimethyl(methylthio)sulfonium tetrafluoroborate 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 GalN(b1-2)Gal(b)-O-octyl
  参考文献：
  名称：

  The 2-N,N-Dibenzylamino Group as a Participating Group in the Synthesis ofβ-Glycosides

  摘要：

  The novel glycosyl donor 2-N,N-dibenzylaminothioglycoside 1 reacts with glycopyranoside alcohols 2, presumably via intermediate 3, to provide 1,2-trans-linked disaccharides 4 in high yield (78-86 %) and with high stereoselectivity. The N-benzyl protecting groups are readily cleaved under normal hydrogenolysis conditions, facilitating the synthesis of oligosaccharides with free amino groups.

  DOI：

  10.1002/(sici)1521-3773(19990201)38:3<346::aid-anie346>3.0.co;2-l
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 在 sodium methylate 、 sodium hydride 、 肼 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 Dibenzyl-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yl)-amine
  参考文献：
  名称：

  The 2-N,N-Dibenzylamino Group as a Participating Group in the Synthesis ofβ-Glycosides

  摘要：

  The novel glycosyl donor 2-N,N-dibenzylaminothioglycoside 1 reacts with glycopyranoside alcohols 2, presumably via intermediate 3, to provide 1,2-trans-linked disaccharides 4 in high yield (78-86 %) and with high stereoselectivity. The N-benzyl protecting groups are readily cleaved under normal hydrogenolysis conditions, facilitating the synthesis of oligosaccharides with free amino groups.

  DOI：

  10.1002/(sici)1521-3773(19990201)38:3<346::aid-anie346>3.0.co;2-l

文献信息

• The 2-N,N-Dibenzylamino Group as a Participating Group in the Synthesis ofβ-Glycosides
  作者：Hailong Jiao、Ole Hindsgaul

  DOI：10.1002/(sici)1521-3773(19990201)38:3<346::aid-anie346>3.0.co;2-l

  日期：1999.2.1

  The novel glycosyl donor 2-N,N-dibenzylaminothioglycoside 1 reacts with glycopyranoside alcohols 2, presumably via intermediate 3, to provide 1,2-trans-linked disaccharides 4 in high yield (78-86 %) and with high stereoselectivity. The N-benzyl protecting groups are readily cleaved under normal hydrogenolysis conditions, facilitating the synthesis of oligosaccharides with free amino groups.