3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azido-2-deoxy-alpha-D-glucopyranosyl chloride | 68733-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azido-2-deoxy-alpha-D-glucopyranosyl chloride
• 英文别名: O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glyucopyranosyl chloride；3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl chloride；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6R)-4-acetyloxy-2-(acetyloxymethyl)-5-azido-6-chlorooxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 68733-23-3
• 化学式: C₂₄H₃₂ClN₃O₁₅
• 分子量: 637.982
• InChiKey: FNVCTOKORTURCA-FHKWVZCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  200
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azido-2-deoxy-alpha-D-glucopyranosyl chloride 在 4-二甲氨基吡啶 、 二甲基硫 、 sodium methylate 、 sodium cyanoborohydride 、 臭氧 、 三苯基膦 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 54.67h， 生成 2-[(2-pyridyl)amino]ethyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 2-[(2-pyridyl)amino]ethyl β-d-lactosaminide and evaluation of its acceptor ability for sialyltransferase: a comparison with 4-methylumbelliferyl and dansyl β-d-lactosaminide

  摘要：

  We report the synthesis Of P-D-lactosaminide with a 2-aminopyridyl group that is linked to a glycosyl tether at the reducing end. This fluorescent disaccharide acts as an acceptor for both alpha-(2 --> 6)- and alpha-(2 --> 3)-sialyltransferases. In addition, the acceptor ability of this disaccharide was evaluated and compared with that Of beta-D-lactosaminide having a dansyl or a 4-methylumbelliferyl group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.015
• 作为产物：
  描述：

  3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate 生成 3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azido-2-deoxy-alpha-D-glucopyranosyl chloride
  参考文献：
  名称：

  LEMIEUX, R. U.;RATCLIFFE, R. M.

  摘要：

  DOI：

文献信息

• Synthesis of a useful anomeric thioacetate of an N-acetyllactosamine derivative and its application
  作者：Koji Matsuoka、Takumi Ohtawa、Hiroshi Hinou、Tetsuo Koyama、Yasuaki Esumi、Shin-Ichiro Nishimura、Ken Hatano、Daiyo Terunuma

  DOI：10.1016/s0040-4039(03)00697-x

  日期：2003.4

  of an N-acetyllactosamine derivative was efficiently synthesized in high yield from the known 2-azido glycosyl chloride using thioacetic acid as a convenient reagent. The synthesis involved not only an SN2 replacement of the chloride by a carbothiolate anion but also a reductive acetamidation of the azide group. Applications of the thioacetate for glycosidation were demonstrated to provide both O- and

  使用硫代乙酸作为方便试剂，从已知的2-叠氮基糖基氯高效高产率地合成了N-乙酰基乳糖胺衍生物的新型异头β-硫代乙酸酯。该合成不仅涉及用硫代硫酸根阴离子对氯化物进行的S N 2取代，而且涉及叠氮化物基团的还原性乙酰胺化。已证明将硫代乙酸酯用于糖苷化可以以高收率提供O-和S-糖苷。此外，两种中间体都产生了包括硫糖苷键的一类新的糖簇。
• Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from
  申请人：Chembiomed Ltd.

  公开号：US04195174A1

  公开（公告）日：1980-03-25

  O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.

  O-乙酰化的糖醛与偏铈铵硝酸盐在存在硝酸钠的情况下反应，产生良好产率的O-乙酰化2-叠氮基-2-脱氧糖基硝酸盐。这些硝酸盐可用于制备2-氨基-2-脱氧糖类，如D-半乳糖胺和乳糖胺。O-乙酰化的2-叠氮基-2-脱氧糖基硝酸盐可被转化为O-乙酰化的2-叠氮基-2-脱氧糖基卤化物，这些卤化物在制备O-乙酰化的2-叠氮基-2-脱氧糖苷时很有用，而后者可以还原为2-氨基-2-脱氧糖苷。特别感兴趣的是合成对应于人类A血型抗原决定簇的2-氨基-2-脱氧糖苷。将这些糖苷连接到固定支持体上可提供有效地吸附血浆中的抗A抗体的免疫吸附剂。
• Chemical and chemoenzymatic synthesis of glycosyl-amino acids and glycopeptides related to Trypanosoma cruzi mucins
  作者：Vanessa Leiria Campo、Ivone Carvalho、Sarah Allman、Benjamin G. Davis、Robert A. Field

  DOI：10.1039/b707772f

  日期：——

  This study describes the synthesis of the alpha- and beta-linked N-acetyllactosamine (Galp-beta-1,4-GlcNAc; LacNAc) glycosides of threonine (LacNAc-Thr). LacNAc-a-Thr was prepared by direct chemical coupling of a 2-azido-2-deoxy-lactose disaccharide donor to a suitable partially protected threonine unit. In contrast, stepwise chemical generation of beta-linked N-acetylglucosamine followed by enzymatic

  本研究描述了苏氨酸 (LacNAc-Thr) 的 α-和β-连接的 N-乙酰乳糖胺 (Galp-β-1,4-GlcNAc; LacNAc) 糖苷的合成。LacNAc-a-Thr 是通过 2-azido-2-deoxy-lactose 二糖供体与合适的部分保护的苏氨酸单元直接化学偶联制备的。相比之下，β-连接的 N-乙酰葡糖胺的逐步化学生成，然后酶促半乳糖基化得到 LacNAc-β-Thr 证明是有效的，而在乙腈中使用 2-叠氮基-2-脱氧-乳糖供体未能得到所需的β-连接二糖苷。这项研究表明，可以克服 GlcNAc 供体对 1,2-反式化学糖基化的固有立体选择，以及牛β-1 的公认偏好，也可以克服用于 β 连接受体底物的 4-半乳糖基转移酶。利用这一知识，合成了基于 T. cruzi 粘蛋白序列的短糖肽片段，Thr-Thr-[LacNAcThr]-Thr-Thr-Gly。概述的所有基于 LacNAc
• Azidochlorination and diazidization of glycals
  申请人：BIOMIRA, INC.

  公开号：EP0340780A2

  公开（公告）日：1989-11-08

  The invention describes a one-pot single step procedure for the azidochlorination or diazidization of glycals, including glycal elements of carbohydrates. Compounds such as 3,4,6-tri-O-benzyl-2-azido-2-deoxy-­alpha-D-galactopyranosyl chloride, and 3,4,6-tri-O-­benzyl-2-azido-2-deoxy-alpha-,beta-D-galactopyranose are prepared from tri-O-benzyl galactal as well as 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-alpha-­galactopyranosyl chloride and 3,6,-di-O-acetyl-4-O-­[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-­azido-2-deoxy-alpha-D-glycopyranosyl chloride from their respective O-acetylated glycal derivatives by the addition of azido chloride which is chemically generated in situ. A method using 3,4,6-tri-O-acetyl-­2-azido-2-deoxy-alpha-D-galacto-pyranosyl chloride for the synthesis of antigenic determinants such as the terminal asialo GM₁(beta-D-Gal (1->3)-beta-D-GalNAc-OR) has been demonstrated. The conversion of the subject synthon into 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-­D-galactopyranosyl bromide and 1,3,4,6-tetra-O-acetyl-­2-azido-2-deoxy-alpha-D-galactopyranose is also described. A further method for the synthetic generation of the Tn antigen (alpha-D-GalNAc-O-L-­serine) is also described.

  本发明描述了一种将糖醛（包括碳水化合物中的糖醛元素）进行叠氮氯化或重氮化的一步法程序。由三-O-苄基半乳糖以及 3,4,6-三-O-乙酰基-2-叠氮-2-脱氧-D-alpha-D-吡喃半乳糖酰氯和 3,4,6-三-O-苄基-2-叠氮-2-脱氧-alpha-,beta-D-吡喃半乳糖制备出 3,4,6-三-O-苄基-2-叠氮-2-脱氧-D-alpha-D-吡喃半乳糖等化合物、一种使用 3,4,6-二-O-乙酰基-4-O-[2,3,4,6-四-O-乙酰基-beta-D-吡喃半乳糖基]-2-叠氮-2-脱氧-D-alpha-D-吡喃糖基氯化物的方法，通过添加原位化学生成的叠氮氯化物，从各自的 O-乙酰化甘醛衍生物中制备出这些物质。一种使用 3,4,6-三-O-乙酰基-2-叠氮-2-脱氧-α-D-吡喃半乳糖酰氯合成抗原决定簇（如末端异构体 GM₁（beta-D-Gal (1->3)-beta-D-GalNAc-OR））的方法已经得到证实。此外，还介绍了将上述合成物转化为 3,4,6-O-三乙酰基-2-叠氮-2-脱氧-alpha-D-吡喃半乳糖溴化物和 1,3,4,6-O-四乙酰基-2-叠氮-2-脱氧-alpha-D-吡喃半乳糖的方法。还描述了合成 Tn 抗原（α-D-半乳糖醛酸-O-L-丝氨酸）的另一种方法。
• US4935503A
  申请人：——

  公开号：US4935503A

  公开（公告）日：1990-06-19