Benzyl 2-(benzyloxycarbonylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside | 77277-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: Benzyl 2-(benzyloxycarbonylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
• 英文别名: benzyl N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate
• CAS: 77277-23-7
• 化学式: C₂₄H₂₉NO₇
• 分子量: 443.497
• InChiKey: BGGIQUJZGRCPJW-LMYCIYFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzyl 2-(benzyloxycarbonylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.5h， 生成 benzyl 3-O-(D-1-carboxyethyl)-2-deoxy-4,6-isopropylidene-2-(tetradecanoylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and immunoadjuvant activities of novel N-acylmuramoyl dipeptides related to the lipid A constituent of the bacterial lipopolysaccharide

  摘要：

  DOI：

  10.1016/s0008-6215(00)85936-4
• 作为产物：
  描述：

  2-benzyloxycarbonylamino-2-deoxy-D-glucose 在 盐酸 、 calcium sulfate 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 0.33h， 生成 Benzyl 2-(benzyloxycarbonylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  脂质A 1-去磷酸衍生物的化学合成

  摘要：

  合成了1-Dephospho大肠杆菌脂质A（），显示与从细菌细胞中分离出的相应衍生物相同。这提供了明确的证据来支持我们最近提出的大肠杆菌脂质A（）的结构。

  DOI：

  10.1016/s0040-4039(00)61962-7

文献信息

• Total Synthesis of<i>Escherichia coli</i>Lipid A, the Endotoxically Active Principle of Cell-Surface Lipopolysaccharide
  作者：Masahiro Imoto、Hiroyuki Yoshimura、Tetsuo Shimamoto、Nobuki Sakaguchi、Shoichi Kusumoto、Tetsuo Shiba

  DOI：10.1246/bcsj.60.2205

  日期：1987.6

  Chemical syntheses are described of polyacylated β(1→6) glucosamine disaccharide 1,4′-bis(phosphate), which corresponds to the proposed structure of E. coli lipid A, and of its dephospho derivatives. The synthetic bisphosphate proved to be identical with the corresponding natural specimen. The chemical structure of lipid A was thus established.

  本文描述了聚酰基化的β(1→6)葡萄糖胺二糖1,4′-二磷酸的化学合成，该化合物对应于拟定的大肠杆菌脂质A的结构，以及其去磷酸衍生物。合成的二磷酸与相应的天然样本相同。因此，脂质A的化学结构得以确立。
• Preparation and Use of Isolactosamine and Intermediates therefor
  申请人：Glycom A/S

  公开号：US20140303363A1

  公开（公告）日：2014-10-09

  The invention relates to providing isolactosamine (Galβ1-3GlcNH 2 , formula 1) and salts thereof in the form of either anomer or mixture thereof, as well as hydrates or solvates of the free base and salts thereof. The synthesis of isolactosamine and its use in the synthesis of lacto-N-biose containing oligosaccharides are also disclosed.

  本发明涉及提供Galβ1-3GlcNH2（式1）及其盐的异构体或混合物的形式，以及自由碱和其盐的水合物或溶剂合物。本发明还公开了Galβ1-3GlcNH2的合成以及其在合成含有乳糖N-生物糖的寡糖中的应用。
• [EN] PREPARATION AND USE OF ISOLACTOSAMINE AND INTERMEDIATES THEREFOR<br/>[FR] PRÉPARATION ET UTILISATION D'ISOLACTOSAMINE ET INTERMÉDIAIRES S'Y RAPPORTANT
  申请人：GLYCOM AS

  公开号：WO2013083136A1

  公开（公告）日：2013-06-13

  The invention relates to providing isolactosamine (Galβ1-3GlcN2, formula 1) and salts thereof in the form of either anomer or mixture thereof, as well as hydrates or solvates of the free base and salts thereof. Isolactosamine derivatives of formula 2, the synthesis of isolactosamine by hydrogenolysis of said derivatives and the use of isolactosamine in the synthesis of lacto-N-biose containing oligosaccharides, through the steps of masking the amino group of isolactosamine with a suitable protecting group, protecting the OH-groups, activating the anomeric position to obtain a lacto-N-biosyl donor and coupling the lacto-N-biosyl donor to a desired sugar moiety, are also disclosed.

  本发明涉及以α或β异构体或其混合形式的盐的形式提供Galβ1-3GlcN2（式1）和其水合物或溶剂化物，以及式2的Isolactosamine衍生物，通过遮盖适当的保护基来保护Isolactosamine的氨基团，保护OH基团，激活异构位置以获得lacto-N-生物糖供体，并将lacto-N-生物糖供体与所需的糖基团偶联，用于合成含有lacto-N-biose的寡糖。同时还公开了通过上述衍生物的氢解来合成Isolactosamine的方法。
• Synthesis and immunoadjuvant activity of acylamino analogs of N-acetylmuramoyl-L-alanyl-D-isoglutamine.
  作者：Hiroyuki OKUMURA、Kei-ichi KAMISANGO、Ikuo SAKI、Yoshiro TANIO、Ichiro AZUMA、Makoto KISO、Akira HASEGAWA、Yuichi YAMAMURA

  DOI：10.1271/bbb1961.46.507

  日期：——

  A variety of long-chain fatty acylamino analogs of N-acetylmuramoyl-L-alanyl-D-isoglutamine (MDP), such as N-(acyl)muramoyl-dipeptides (1) and N-acetyl-6-(acylamino)-6-deoxymuramoyl-dipeptides (2), were synthesized to examine their immunological activities. All the N-(acyl)muramoyl-L-alanyl-D-isoglutamines (1) were active as adjuvant on the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs. N-(3-Hydroxy-2-tetradecyloctadecanoylamino)muramoyl-L-alanyl-D-isoglutamine (1d) and N-acetyl-6-deoxy-6-(3-hydroxy-2-docosylhexacosanoylamino)murarnoyl-L-alanyl-, -L-valyl-, and -L-seryl-D-isoglutamines (2) showed antitumor activity by suppressing tumor (Meth-A fibrosarcoma) growth in syngeneic BALB/c mice.

  研究人员合成了多种 N-乙酰基缪拉莫伊-L-丙氨酰-D-异谷氨酰胺（MDP）的长链脂肪酰氨基类似物，如 N-（酰基）缪拉莫伊二肽（1）和 N-乙酰基-6-（酰氨基）-6-脱氧缪拉莫伊二肽（2），以考察它们的免疫活性。所有 N-（酰基）喃甲酰-L-丙氨酰-D-异谷氨酸（1）作为佐剂对诱导豚鼠对偶氮苯胂酸-N-乙酰-L-酪氨酸的迟发型超敏反应均有活性。N-(3-羟基-2-十四烷基十八碳酰氨基)喃甲酰-L-丙氨酰-D-异谷氨酰胺（1d）和 N-乙酰基-6-脱氧-6-(3-羟基-2-二十二烷基六碳酰氨基)喃甲酰-L-丙氨酰-L-缬氨酰-和 N-乙酰基-6-脱氧-6-(3-羟基-2-二十二烷基六碳酰氨基)喃甲酰-L-丙氨酰-D-异谷氨酰胺（1d）对豚鼠迟发型超敏反应的诱导具有活性、-L-缬氨酰-和-L-丝氨酰-D-异谷氨酰胺（2）通过抑制合成 BALB/c 小鼠体内肿瘤（Meth-A 纤维肉瘤）的生长而显示出抗肿瘤活性。
• IMOTO, MASAHIRO;YOSHIMURA, HIROYUKI;SHIMAMOTO, TETSUO;SAKAGUCHI, NOBUKI;K+, BULL. CHEM. SOC. JAP., 60,(1987) N 6, 2205-2214
  作者：IMOTO, MASAHIRO、YOSHIMURA, HIROYUKI、SHIMAMOTO, TETSUO、SAKAGUCHI, NOBUKI、K+

  DOI：——

  日期：——