4-O-Acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 125946-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-Acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate
• CAS: 125946-68-1
• 化学式: C₃₂H₂₉Cl₃N₂O₈
• 分子量: 675.95
• InChiKey: RAMMTVULKGXSRP-YFQBHRANSA-N

物化性质

• 沸点：
  698.7±65.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  124.45
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-O-Acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 在 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Stereocontrolled synthesis of chitosan dodecamer

  摘要：

  DOI：

  10.1016/0008-6215(93)84095-n
• 作为产物：
  描述：

  allyl-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 在 吡啶 、 sodium acetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 4-O-Acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein

  摘要：

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(90)84222-g

文献信息

• Synthesis of 2-aminoethyl glycosides of chitooligosaccharides
  作者：O. N. Yudina、Yu. E. Tsvetkov、N. E. Nifantiev

  DOI：10.1007/s11172-015-1250-6

  日期：2015.12

  2-Aminoethyl glycosides of chitotriose, chitopentaose, and chitoheptaose were synthesized. The successive extension of the oligosaccharide chain by two monosaccharide residues was carried out using a monosaccharide acceptor and a disaccharide donor, in which amino groups were protected by phthaloyl groups, benzyl moieties were used as a permanent protection for the hydroxy groups at C(3) and C(6), and acetyl or chloroacetyl groups were employed as a temporary protection for the hydroxy group at C(4).

  合成了2-氨基乙基壳三糖、壳五糖和壳七糖。通过使用单糖受体和二糖供体，逐步将寡糖链延长两个单糖残基，其中氨基通过邻苯二甲酰基保护，C(3)和C(6)位的羟基通过苄基作为永久保护，C(4)位的羟基通过乙酰基或氯乙酰基作为临时保护。
• Synthetic Studies on Sialoglycoconjugates 90: Total Synthesis of Sulfated Glucuronyl Paraglobosides
  作者：Yukihiro Isogai、Tomoko Kawase、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1080/07328309608005705

  日期：1996.11

  stereocontrolled glycosidation, methyl (4-O-acetyl-2-O-benzoyl-3-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate)uronate (8) was prepared from methyl [2-(trimethylsilyl)ethyl β-D-glucopyranosid]uronate (3) via selective 4-O-acetylation, 2-O-benzoylation, 3-O-levulinoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation. The glycosylation of 8 with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-

  已经合成了3- O-磺基葡萄糖醛酸酰基副球糖苷衍生物（五糖）。设计用于在最后一步有效，立体控制苷化的简便的硫酸化重要的中间体，甲基（4- ø -乙酰基-2- ø -苯甲酰基-3- ö -levulinoyl-α-d吡喃葡糖基三氯乙酰亚胺酯）糖醛酸（8）为由[2-（三甲基甲硅烷基）乙基β-D-吡喃葡萄糖苷]尿酸酯（3）经选择性的4- O-乙酰化，2- O-苯甲酰化，3- O-乙酰丙酰化，去除2-（三甲基甲硅烷基）乙基制备和亚氨酸盐的形成。8的糖基化用三甲基甲硅烷基三氟甲磺酸酯与2-（三甲基甲硅烷基）乙基2,4,6-三-O-苄基-β-D-吡喃半乳糖苷（9）得到2-（三甲基甲硅烷基）乙基O-（甲基4 - O-乙酰基-2- O -苯甲酰基-3- O-乙酰丙酰基-β-D-吡喃葡萄糖基尿酸酯）-（1→3）-2,4,6-三-O-苄基-β-D-吡喃半乳糖苷（10），通过除去苄基，苯甲酰化，去除2-（三甲基
• Stereoselective synthesis of a core glycoheptaose of bisected biantenarry complex type glycan of glycoproteins
  作者：Fumito Yamazaki、Tomoo Nukada、Yukishige Ito、Susumu Sato、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)99376-6

  日期：1989.1

  A stereocontrolled synthesis of a core glycoheptaose of “bisected” complex type glycans of a glycoprotein was achieved by use of stereoselective glycosylation.

  通过使用立体选择性糖基化来实现糖蛋白“二等分”复杂类型聚糖的核心糖庚糖的立体控制合成。
• Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins
  作者：Peng Wang、Jun Wang、TianTian Guo、Yingxia Li

  DOI：10.1016/j.carres.2010.01.002

  日期：2010.3

  Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-beta-D-glucosamine, and (1 -> 4)-linked and (1 6)-linked N-acetyl-beta-D-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by (1)H NMR and (13)C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl beta-D-GluNAc showed significant cytotoxicity against HL-60 and BGC-823. (C) 2010 Published by Elsevier Ltd.
• YAMAZAKI, FUMITO;KITAJIMA, TOHRU;NUKADA, TOMOO;ITO, YUKISHIGE;OGAWA, TOMO+, CARBOHYDR. RES. , 201,(1990) N, C. 15-30
  作者：YAMAZAKI, FUMITO、KITAJIMA, TOHRU、NUKADA, TOMOO、ITO, YUKISHIGE、OGAWA, TOMO+

  DOI：——

  日期：——