phenyl 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl-D-thioglucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl-D-thioglucopyranoside
• 英文别名: 2,3,4-tri-O-benzyl-6-O-trichloroethoxycarbonyl phenyl thioglucoside；2,2,2-trichloroethyl [(2R,3R,4S,5R)-3,4,5-tris(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl carbonate
• 化学式: C₃₆H₃₅Cl₃O₇S
• 分子量: 718.095
• InChiKey: NLPHVFMFQZPHKP-BKJHVTENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  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

• Synthesis Based on Affinity Separation (SAS): Separation of Products Having Barbituric Acid Tag from Untagged Compounds by Using Hydrogen Bond Interaction
  作者：San-Qi Zhang、Koichi Fukase、Minoru Izumi、Yoshiyuki Fukase、Shoichi Kusumoto

  DOI：10.1055/s-2001-13392

  日期：——

  A new method is described for affinity purification of synthetic compounds based on molecular recognition between bis(2,6-diaminopyridine)amide of isophthalic acid and a barbituric acid derivative. The desired compounds possessing the barbituric acid derivative as a tag were readily isolated from the reaction mix- ture by the following procedure. After each reaction cycle, the reac- tion mixture was

  描述了一种基于间苯二甲酸的双 (2,6-二氨基吡啶) 酰胺和巴比妥酸衍生物之间的分子识别亲和纯化合成化合物的新方法。具有作为标签的巴比妥酸衍生物的所需化合物可通过以下程序容易地从反应混合物中分离。在每个反应循环后，将反应混合物施加到具有间苯二甲酸双（2,6-二氨基吡啶）酰胺作为人工受体的聚苯乙烯柱上。带有巴比妥酸标签的化合物被选择性地吸附在色谱柱上，而没有标签的其他杂质如过量的试剂和副产物被洗掉。随后用 CH2Cl2-MeOH (1:1) 解吸得到所需的高纯度化合物。
• Egusa, Kenji; Fukase, Koichi; Nakai, Yoshihiko, Synlett, 2000, # 1, p. 27 - 32
  作者：Egusa, Kenji、Fukase, Koichi、Nakai, Yoshihiko、Kusumoto, Shoichi

  DOI：——

  日期：——
• 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 Oxidatively Removable Linker and Its Application to α-Selective Solid-Phase Oligosaccharide Snythesis on a Macroporous Polystyrene Support
  作者：Koichi Fukase、Yoshihiko Nakai、Kenji Egusa、John A. Porco Jr.、Shoichi Kusumoto

  DOI：10.1055/s-1999-2779

  日期：1999.7
• 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.