tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-4,6-isopropylidene-α-D-galactopyranosyl)-<(1->4)-O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)>₂-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside | 120654-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-4,6-isopropylidene-α-D-galactopyranosyl)-<(1->4)-O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)>₂-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3-[[(4aR,6R,7R,8S,8aS)-2,2-dimethyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-6-[(2R,3S,4S,5R,6R)-2-(acetyloxymethyl)-6-[(2R,3S,4S,5R,6S)-2-(acetyloxymethyl)-6-[tert-butyl(diphenyl)silyl]oxy-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 120654-55-9
• 化学式: C₁₀₅H₁₁₈O₂₄Si
• 分子量: 1792.16
• InChiKey: GTCVLYCASBUYMM-XMWUAHQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.14
• 重原子数：
  130
• 可旋转键数：
  44
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  245
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-4,6-isopropylidene-α-D-galactopyranosyl)-<(1->4)-O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)>₂-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside 在 溶剂黄146 作用下， 反应 0.5h， 以91.5%的产率得到tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-α-D-galactopyranosyl)-<(1->4)-O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)>₂-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective total synthesis of dodecagalacturonic acid, a phytoalexin elicitor of soybean

  摘要：

  O-(alpha-D-Galactopyranosyluronic acid)-[(1----4)-O-(alpha-D-galactopyranosyluronic acid)]10-D-galactopyranuronic acid (1), an endogenous elicitor of the phytoalexin of soybean, was synthesized by way of highly stereoselective glycosylations that involved glycosyl fluorides as the donors and oxidation of the twelve primary hydroxyl groups in the alpha-(1----4)-linked galactododecaoside derivative.

  DOI：

  10.1016/0008-6215(90)80135-p
• 作为产物：
  描述：

  tert-butyldiphenylsilyl O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside 、 O-(2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyl fluoride 在 4 A molecular sieve 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以77.4%的产率得到tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-4,6-isopropylidene-α-D-galactopyranosyl)-<(1->4)-O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)>₂-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective total synthesis of dodecagalacturonic acid, a phytoalexin elicitor of soybean

  摘要：

  O-(alpha-D-Galactopyranosyluronic acid)-[(1----4)-O-(alpha-D-galactopyranosyluronic acid)]10-D-galactopyranuronic acid (1), an endogenous elicitor of the phytoalexin of soybean, was synthesized by way of highly stereoselective glycosylations that involved glycosyl fluorides as the donors and oxidation of the twelve primary hydroxyl groups in the alpha-(1----4)-linked galactododecaoside derivative.

  DOI：

  10.1016/0008-6215(90)80135-p

文献信息

• NAKAHARA, YOSHIAKI;OGAWA, TOMOYA, CARBOHYDR. RES., 205,(1990) C. 147-159
  作者：NAKAHARA, YOSHIAKI、OGAWA, TOMOYA

  DOI：——

  日期：——