allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine | 155177-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine
• CAS: 155177-85-8
• 化学式: C₃₄H₃₄N₄O₉
• 分子量: 642.665
• InChiKey: ATGZOEHOWJYRDV-WJYGJJSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  170.54
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  人血粘蛋白中存在的A型血型糖肽的立体选择性合成

  摘要：

  N，N-二甲基-O-（2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖基）-（1-> 3）-O-[（α-L-呋喃核糖基）-（1-> 2） ] -O-（β-D-吡喃半乳糖基）-（1-> 3）-O-（2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖基）-（1-> 3）-L-丝氨酸首次合成了人血型A卵巢粘蛋白中复杂的聚糖糖蛋白中的核心I糖四糖基肽结构和主要亚结构。标题化合物是通过以下关键操作合成完成的：α-GalNAc-（1-> 3）-Gal合成子的区域和立体控制结构，产生α-GalN3-（1-> 3）的立体选择性糖基化）-Ser糖肽合成子和朝向受体的α-选择性岩藻糖基化，该糖基化来自后两个合成子的糖基化。后者的另一种选择，

  DOI：

  10.1016/0008-6215(94)00362-j
• 作为产物：
  描述：

  2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-β-D-galactopyranosyl fluoride 在 氟化铵 、 二氯二茂锆 、 4 A molecular sieve 、 silver perchlorate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine
  参考文献：
  名称：

  人血粘蛋白中存在的A型血型糖肽的立体选择性合成

  摘要：

  N，N-二甲基-O-（2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖基）-（1-> 3）-O-[（α-L-呋喃核糖基）-（1-> 2） ] -O-（β-D-吡喃半乳糖基）-（1-> 3）-O-（2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖基）-（1-> 3）-L-丝氨酸首次合成了人血型A卵巢粘蛋白中复杂的聚糖糖蛋白中的核心I糖四糖基肽结构和主要亚结构。标题化合物是通过以下关键操作合成完成的：α-GalNAc-（1-> 3）-Gal合成子的区域和立体控制结构，产生α-GalN3-（1-> 3）的立体选择性糖基化）-Ser糖肽合成子和朝向受体的α-选择性岩藻糖基化，该糖基化来自后两个合成子的糖基化。后者的另一种选择，

  DOI：

  10.1016/0008-6215(94)00362-j

文献信息

• Synthesis of a glycotetraosyl serine, a partial structure of an ovarian cyst mucin glycoprotein of blood group A activity
  作者：Wallace M. Macindoe、Hiroyuki Iijima、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/0040-4039(94)88332-7

  日期：1994.3

  A glycotetraosyl serine containing blood group A determinant tetrasaccharide and its properly protected equivalent were synthesized in a regio- and stereocontrolled manner.

  以区域和立体控制的方式合成了含糖四糖基丝氨酸的血型A决定簇四糖及其适当保护的等同物。
• Solid-Phase Synthesis of Core 8<i>O</i>-Glycan-Linked MUC5AC Glycopeptide
  作者：Makoto MAEMURA、Atsushi OHGAKI、Yuko NAKAHARA、Hironobu HOJO、Yoshiaki NAKAHARA

  DOI：10.1271/bbb.69.1575

  日期：2005.1

  The benzyl-protected disaccharide building blocks of core 8 O-glycan (15a/15b) for glycopeptide were stereoselectively synthesized by two glycosidation reactions with the glycosyl fluoride method. The building blocks were utilized in the solid-phase synthesis of a glycopeptide carrying two O-glycans with the consensus sequence of the tandem-repeat domain of MUC5AC. The synthetic glycopeptide was detached from the resin with reagent K, and subsequent debenzylation under conditions of low-acidity TfOH afforded glycopeptide 2. The synthetic sample will be used as a suitable standard in studies of the physicochemical or immunochemical characterization of mucin glycoforms.

  利用糖基化氟化物方法，通过两个糖苷化反应立体选择性地合成了用于糖肽的核心 8 O-聚糖（15a/15b）的苄基保护二糖构件。利用这些构件固相合成了含有两个 O-聚糖的糖肽，其序列与 MUC5AC 的串联重复结构域的共识序列一致。合成的糖肽用试剂 K 从树脂中分离出来，随后在低酸 TfOH 条件下进行脱苄基反应，得到糖肽 2。该合成样本将在粘蛋白糖形的物理化学或免疫化学表征研究中用作合适的标准。
• Solid-phase synthesis of the B-chain of human α2HS glycoprotein
  作者：Yoshiaki Nakahara、Yuko Nakahara、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0008-6215(98)00142-6

  日期：1998.7

  The B-chain of human alpha 2HS glycoprotein 1, a heptacosapeptide carrying a trisaccharide (sialyl T) side chain, was synthesized. Prior to the Fmoc-based solid-phase synthesis of the glycopeptide, the benzyl-protected glycosyl serine building block 6 was prepared via beta-stereoselective glycosylation of the 2-azido-2-deoxygalactosyl serine 11 with the sialyl galactosyl trichloroacetimidate 9. An automated peptide synthesizer was efficiently used for the elongation of the entire peptide chain except for the coupling with 6. The synthesized glycopeptide was cleaved from the resin by the TFA method. The resultant mixture of the benzylated glycopeptides was treated with TMSOTf-thioanisole in TFA and then with aq NaHCO3 and 1,4-dithiothreitol to give 1. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment
  作者：Zhi-Guang Wang、Xu-Fang Zhang、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0968-0896(96)00172-1

  日期：1996.11

  Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide la. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides. Copyright (C) 1996 Elsevier Science Ltd
• Stereoselective synthesis of benzyl-protected β-galactosides by propionitrile-mediated glycosylation
  作者：Akiharu Ueki、Masafumi Hirota、Yuta Kobayashi、Keiko Komatsu、Yutaka Takano、Michio Iwaoka、Yuko Nakahara、Hironobu Hojo、Yoshiaki Nakahara

  DOI：10.1016/j.tet.2008.01.029

  日期：2008.3

  beta-Selective galactosylation was studied using a series of 2-O-benzylated phenyl 1-thio-galactosides and glycosyl acceptors in propionitrile with BSP-TTBP-Tf2O. The glycosylation enabled us to synthesize useful precursors of N-acetyllactosamine and core 1 O-glycoserine derivatives in a highly convergent manner. (c) 2008 Elsevier Ltd. All rights reserved.