methyl 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl-α-D-glucopyranosyl-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl-α-D-glucopyranosyl-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；[(2R,3R,4S,5R,6S)-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl 2,2,2-trichloroethyl carbonate
• 化学式: C₅₈H₆₁Cl₃O₁₃
• 分子量: 1072.47
• InChiKey: VWIIUTVDGQCDMY-AOTKYVILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  74
• 可旋转键数：
  27
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  13

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷	methyl 2,3,4-tri-O-benzyl-D-glucopyranoside	53008-65-4	C28H32O6	464.558
  ——	phenyl 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl-D-thioglucopyranoside	——	C36H35Cl3O7S	718.095

反应信息

• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 phenyl 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl-D-thioglucopyranoside 在 亚碘酰苯 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以82%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl-α-D-glucopyranosyl-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  A novel method for stereoselective glycosidation with thioglycosides: Promotion by hypervalent iodine reagents prepared from PhIO and various acids.

  摘要：

  Combinations of iodosobenzene (PhIO) and various acids effectively promote glycosidation using thioglycosides as glycosyl donors. beta-Selective glucosidation was effected by use of TfOH, Tf(2)O, TMSOTf, Sn(OTf)(2), and Yb(OTf)(3) as catalysts with 2-O-benzoylated or 2-O-benzylated donors by virtue of either the neighboring group participation or the solvent effect of acetonitrile, respectively. Combinations of PhIO with SnCl2-AgClO4, SnCl4-AgClO4, BiCl3-AgClO4, and SbCl3-AgClO4 in ether were advantageous for alpha-glucosidation, where 2,2,2-trichloroethoxycarbonyl group introduced at the 6-position of a 2-O-benzylated donor remarkably increased alpha-selectivity.

  DOI：

  10.1016/s0040-4020(96)00057-9

文献信息

• A stereoselective glycosidation using thioglycosides, activation by combination of N-bromosuccinimide and strong acid salts
  作者：Koichi Fukase、Atsushi Hasuoka、Ikuko Kinoshita、Yutaka Aoki、Shoichi Kusumoto

  DOI：10.1016/0040-4020(95)98690-j

  日期：1995.4

  A stereoselective glycosidation with thioglycosides was effected under mild and neutral conditions by combined use of N-bromosuccinimide (NBS) and a catalytic amount of various strong acid salts. A combination of NBS with Ph(2)IOTf, Bu(4)NOTf, or Bu(4)NClO(4) was advantageous for beta-selective glucosidation with 2-O-acylated or 2-O-benzylated donors by virtue of either the neighboring group participation or the known solvent effect of nitrile, respectively. alpha-Selective glucosidation was effected by the use of a 2-O-benzylated donor in the presence of LiClO4 or LiNO3 as a catalyst in ether, Addition of silica gel to the reaction mixture increased both the a-selectivity and reaction rate.
• A novel method for stereoselective glycosidation with thioglycosides: Promotion by hypervalent iodine reagents prepared from PhIO and various acids.
  作者：Koichi Fukase、Ikuko Kinoshita、Takeshi Kanoh、Yoshihiko Nakai、Atsushi Hasuoka、Shoichi Kusumoto

  DOI：10.1016/s0040-4020(96)00057-9

  日期：1996.3

  Combinations of iodosobenzene (PhIO) and various acids effectively promote glycosidation using thioglycosides as glycosyl donors. beta-Selective glucosidation was effected by use of TfOH, Tf(2)O, TMSOTf, Sn(OTf)(2), and Yb(OTf)(3) as catalysts with 2-O-benzoylated or 2-O-benzylated donors by virtue of either the neighboring group participation or the solvent effect of acetonitrile, respectively. Combinations of PhIO with SnCl2-AgClO4, SnCl4-AgClO4, BiCl3-AgClO4, and SbCl3-AgClO4 in ether were advantageous for alpha-glucosidation, where 2,2,2-trichloroethoxycarbonyl group introduced at the 6-position of a 2-O-benzylated donor remarkably increased alpha-selectivity.