1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose | 55287-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose
• 英文别名: 1,2,3-tri-O-acetyl-D-arabinofuranose；5-hydroxy arabinose；[(2R,3R,4S)-4,5-diacetyloxy-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 55287-20-2
• 化学式: C₁₁H₁₆O₈
• 分子量: 276.243
• InChiKey: BGAWRLZKVIFLKK-NFLHVTIKSA-N

物化性质

• 沸点：
  370.0±42.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose 在 palladium on activated charcoal sodium azide 、 水 、 氢气 、 sodium methylate 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 78.5h， 生成 5-amino-5-deoxy-D-arabinopyranose TFA salt
  参考文献：
  名称：

  Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-d-arabinopyranosyl)-2-deoxy-1,6-dithio-β-d-glucopyranoside: a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide

  摘要：

  A novel pseudo-disaccharide having an imino sugar residue at the non-reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with ethyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-1,6-dithio-beta-D- glucopyranoside in the presence of TsOH gave exclusively the corresponding 1,2-cis-linked thioglycoside. The interglycosidic linkage proved stable enough under conditions for the deprotection of the N-Boc group with TFA. This pseudodisaccharide was unstable at pH > 5, but stable at lower pH. The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6-dithio-beta-D-glucopyranoside in an acidic buffer solution.

  DOI：

  10.1016/s0008-6215(99)00253-0
• 作为产物：
  描述：

  1,2,3-tri-O-acetyl-5-O-triphenylmethyl-D-arabinofuranose 在 溶剂黄146 作用下， 反应 1.17h， 以66%的产率得到1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose
  参考文献：
  名称：

  从d-阿拉伯糖轻松合成5-thio-1-fucose和5-thio-d-阿拉伯糖

  摘要：

  摘要由5-O-三苯甲基-d-阿拉伯糖基呋喃糖或d-阿拉伯糖二乙基二硫缩醛在C-5上一键延伸，合成了11个步骤的5-巯基-呋喃葡萄糖四乙酸酯。实现了将醚中的MeLi高度非对映选择性地添加到1,2-O-异亚丙基-β-d-阿拉伯糖基戊二醛-1,4-呋喃糖衍生物中，得到相应的6-脱氧-β-d-呋喃糖异构体。良品率高。通过在HMPA中用KSAc取代5-甲苯磺酸酯并反转构型，将硫原子引入6-脱氧-d-呋喃呋喃糖衍生物的C-5处，得到5-硫-1-呋喃葡萄糖。还由6-脱氧-β-d-呋喃糖衍生物制备3-O-取代的-1-岩藻糖衍生物。5-硫代-1-呋喃糖的5-脱甲基类似物5-噻吩基-阿拉伯吡喃喃糖四乙酸酯也由5个步骤由5-O-三苯甲基-d-阿拉伯呋喃糖合成。

  DOI：

  10.1016/0008-6215(95)00323-1

文献信息

• A Simple Synthesis of C-8 Modified 2-Keto-3-deoxy-d-manno-octulosonic Acid (KDO) Derivatives
  作者：Milton Kiefel、Renee Winzar、Jessica Philips

  DOI：10.1055/s-0029-1219356

  日期：2010.3

  This paper describes a simple and efficient method with which to prepare C-8 modified 2-keto-3-deoxy-d-manno-octulosonic acid (KDO) derivatives from C-5 modified arabinose derivatives.

  本文描述了一种简单高效的方法，可以从C-5修饰的阿拉伯糖衍生物制备C-8修饰的2-酮-3-脱氧-d-甘露-壬酸（KDO）衍生物。
• Synthesis of 1,5-dideoxy-1,5-imino-d-arabinitol (5-nor-l-fuco-1-deoxynojirimycin) and its application for the affinity purification and characterisation of α-l-fucosidase
  作者：Günter Legler、Arnold E. Stütz、Hermann Immich

  DOI：10.1016/0008-6215(95)00032-o

  日期：1995.7

  Abstract The title, 1,5-dideoxy-1,5-imino- d -arabinitol (2), was synthesized in seven steps from d - arabinose with 5-azido-5-deoxy- d -arabinofuranose as key intermediate and 40% overall yield. An affinity procedure employing the N-carboxypentyl derivative of 2 linked to aminohexyl agarose permitted the isolation of pure α- l - fucosidase from bovine kidney homogenate in two steps. Inhibition constants

  摘要以d-阿拉伯糖为主要原料，以5-叠氮基5-deoxy-d-阿拉伯呋喃糖为原料，经7个步骤合成了1,5-dideoxy-1,5-imino-d-arabinitol（2）。总产量。利用连接到氨基己基琼脂糖上的2的N-羧基戊基衍生物的亲和程序，可以分两步从牛肾脏匀浆中分离出纯的α-1-岩藻糖苷酶。纯化酶的抑制常数2为39μM（pH 5.0）至3μM（pH 7.0），在这些pH值下，对fuco -1-脱氧野oji霉素（1）的抑制作用约为KI的1,500倍。d-甘露聚糖和l-gulo-1-脱氧野oji霉素的K1值也表明了甲基1对抑制作用的较大贡献。1，2对K1的pH依赖性 和其他基本类似物与1-岩藻糖的K1非常相似（pH 5.0时为205μM，pH 7.0时为25μM）。另一方面，对硝基苯基α-1-岩藻糖苷的KM和对于甲基α-1-岩藻糖苷的K1随pH的变化很小。相对于不同的pH依赖性，相对于甲
• Synthesis of putative chain terminators of mycobacterial arabinan biosynthesis
  作者：Iain A. Smellie、Sanjib Bhakta、Edith Sim、Antony J. Fairbanks

  DOI：10.1039/b704788f

  日期：——

  The synthesis of a variety of arabinose derivatives that have been modified at C-5 was achieved from D-arabinose. The 5-fluoro and 5-methoxy compounds were converted into the corresponding farnesyl phosphodiesters as putative chain terminators of mycobacterial arabinan biosynthesis. Biological testing of these materials revealed no effective anti-mycobacterial activity.

  以 D-阿拉伯糖为原料，合成了多种 C-5 修饰的阿拉伯糖衍生物。5 -氟和 5 -甲氧基化合物被转化为相应的法呢基磷酸二酯，作为霉菌阿拉伯糖生物合成的假定链终止器。对这些材料进行的生物测试表明，它们没有有效的抗霉菌活性。
• Isoniazid Conjugates with D-Arabinofuranose
  作者：O. V. Andreeva、V. E. Kataev

  DOI：10.1134/s1070363218070101

  日期：2018.7

  Glycoconjugates with isoniazid attached to the hydroxy group at the C-5 atom of D-arabinofuranose via the spacers differing in length have been synthesized.