3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 125946-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• 英文别名: 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-α/β-D-glucopyranosyl trichloroacetimidate；[(2S,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trichloroethanimidate
• CAS: 125946-65-8
• 化学式: C₃₇H₃₃Cl₃N₂O₇
• 分子量: 724.037
• InChiKey: HSSIOCANGZYGLD-NRLOGRAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107.38
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 乙二胺 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 53.5h， 生成 8-azidooctyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→3)-4-O-benzyl-6-deoxy-β-D-ido-heptopyranoside
  参考文献：
  名称：

  空肠弯曲菌菌株 CG8486 荚膜多糖的含 6-脱氧-d-碘-吡喃庚糖片段的合成

  摘要：

  是胃肠道疾病的重要原因，它们产生的荚膜多糖（CPS）是关键的毒力因子和疫苗开发的目标。我们在此报告了 CG8486 菌株 CPS 的两个片段的合成，其中包含罕见的 6-脱氧-吡喃庚糖残基，并且在一个靶标中包含二甲基氨基磷酸酯 (MeOPN) 基序。该合成方法的特点是通过与 β---吡喃庚糖苷供体进行糖基化，然后进行一锅连续 C-2 和 C-3 倒置，立体选择性构建 β---吡喃庚糖苷键。在合成过程中，我们发现了许多关于 6-脱氧-吡喃庚糖环、连接两个单糖的糖苷键和 MeOPN 基团的有趣构象效应。

  DOI：

  10.1016/j.carres.2024.109058
• 作为产物：
  描述：

  allyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 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 36.0h， 生成 3,4,6-tri-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

• 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 of the <i>Campylobacter jejuni</i> 81 <b>‐</b> 176 Strain Capsular Polysaccharide Repeating Unit Reveals the Absolute Configuration of its <i>O</i> ‐Methyl Phosphoramidate Motif
  作者：V. Narasimharao Thota、Michael J. Ferguson、Ryan P. Sweeney、Todd L. Lowary

  DOI：10.1002/anie.201810222

  日期：2018.11.19

  the absolute stereochemistry at this atom has been undefined. We report the synthesis of the three repeating units found in C. jejuni 81‐176 CPS; one of these possesses a MeOPN group. In the course of these studies we established that the stereochemistry of the phosphorus atom in this MeOPN group is R. These studies represent the first unequivocal proof of stereochemistry of this group in any C. jejuni

  所述Ô甲基氨基磷酸酯（MeOPN）基序在所有的≈70％荚膜多糖（CPS）的一个非化学计量的修改空肠弯曲菌菌株。空肠弯曲杆菌的感染导致食源性疾病，它们产生的CPS是关键的毒力因子。这些CPS中的MeOPN磷原子是立体异构的，是单一的立体异构体。然而，迄今为止，该原子的绝对立体化学尚未确定。我们报告了空肠弯曲杆菌81-176 CPS中三个重复单元的合成；其中之一拥有MeOPN小组。在这些研究过程中，我们确定了该MeOPN基团中磷原子的立体化学是R。这些研究代表了空肠弯曲杆菌CPS中该组立体化学的第一个明确证据。预期所产生的化合物将是针对这种结构有趣的修饰的功能和生物合成进行研究的有用工具，到目前为止，这种修饰仅在弯曲杆菌中才能鉴定出来。
• Regio- and stereo-controlled synthesis of 6-deoxy-β-<scp>d</scp>-<i>ido</i>-heptopyranosides related to <i>Campylobacter jejuni</i> HS:4
  作者：Saba Homayonia、Pengfei Zhang、Ping Zhang、Chang-Chun Ling

  DOI：10.1039/d3ob00683b

  日期：——

  antibodies against the CPS structures of C. jejuni HS:4 is an attractive strategy. The 6-deoxy-ido-configuration of the heptose combined with its β-anomeric configuration makes the chemical synthesis of the disaccharide very challenging. Here, we report an efficient synthesis to obtain the key repeating disaccharide and its analog in reverse order plus a trisaccharide. Our synthesis features a highly efficient

  空肠弯曲菌是一种细菌病原体，每年在全世界引起数亿例食源性胃肠炎病例。这种细菌引起的感染还与多种形式的感染后自身免疫后遗症有关，这些后遗症可能非常严重，包括危及生命的吉兰-巴利综合征。空肠弯曲菌 HS:4的荚膜多糖 (CPS)由非常独特的重复二糖单元组成，其特征是 β-1,4-连接的 6-脱氧-β- D- ido -庚吡喃糖和N-乙酰基- β- D-葡萄糖胺。引发针对空肠弯曲菌HS:4的 CPS 结构的碳水化合物特异性抗体是一种有吸引力的策略。6-脱氧-庚糖的ido构型与其 β-异头构型相结合，使得二糖的化学合成非常具有挑战性。在这里，我们报告了一种有效的合成方法，以获得关键的重复二糖及其逆序类似物加上三糖。我们的合成方法通过中间体 2,3-anHydro-β- D - talo - 高效、一步立体和区域选择性地将 β- D -半乳糖-吡喃庚糖苷转化为 6-脱氧-β- D - ido -吡喃庚糖苷。吡喃庚糖苷。
• 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：——
• Synthesis of N -glycan units for assessment of substrate structural requirements of N -acetylglucosaminyltransferase III
  作者：Shinya Hanashima、Hiroaki Korekane、Naoyuki Taniguchi、Yoshiki Yamaguchi

  DOI：10.1016/j.bmcl.2014.07.074

  日期：2014.9

  N-Acetylglucosaminyltransferase (GnT) III is a glycosyltransferase which produces bisected N-glycans by transferring GlcNAc to the 4-position of core mannose. Bisected N-glycans are involved in physiological and pathological processes through the functional regulation of their carrier proteins. An understanding of the biological functions of bisected glycans will be greatly accelerated by use of specific inhibitors of GnT-III. Thus far, however, such inhibitors have not been developed and even the substrate-binding mode of GnT-III is not fully understood. To gain insight into structural features required of the substrate, we systematically synthesized four N-glycan units, the branching parts of the bisected and non-bisected N-glycans. The series of syntheses were achieved from a common core trimannose, giving bisected tetra-and hexasaccharides as well as non-bisected tri- and pentasaccharides. A competitive GnT-III inhibition assay using the synthetic substrates revealed a vital role for the Man beta(1-4) GlcNAc moiety. In keeping with previous reports, GlcNAc at the alpha 1,3-branch is also involved in the interaction. The structural requirements of GnT-III elucidated in this study will provide a basis for rational inhibitor design. (C) 2014 Elsevier Ltd. All rights reserved.