乙基2-乙酰氨基-2-脱氧- | 122331-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙基2-乙酰氨基-2-脱氧-
• 中文别名: 乙酰胺基-2-脱氧-β-D-硫代吡喃葡萄糖苷
• 英文名称: Ethyl 1-sulfanyl-(2-acetamido-2-deoxy)-O-β-D-glucopyranoside
• 英文别名: methyl 2-acetylamino-2-deoxy-1-thio-β-D-glucopyranoside；ethyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside；N-(S-ethyl-1-thio-β-D-glucopyranose-2-yl)-acetamide；N-(S-Aethyl-1-thio-β-D-glucopyranose-2-yl)-acetamid；N-[(2S,3R,4R,5S,6R)-2-Ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 122331-70-8
• 化学式: C₁₀H₁₉NO₅S
• 分子量: 265.331
• InChiKey: GLDKHCZSFYJVMF-IGORNWKESA-N

物化性质

• 熔点：
  216-218°C
• 沸点：
  566.9±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙基2-乙酰氨基-2-脱氧- 在 α-galactosidase II from Aspergillus oryzae 、 β-galactosidase from Bacillus circulans acetate buffer (pH: 5.0) 、 citrate-phosphate buffer (pH: 5.0) 作用下， 反应 27.0h， 生成
  参考文献：
  名称：

  Glycosidase-catalysed synthesis of oligosaccharides: a one step synthesis of lactosamine and of the linear B type 2 trisaccharide α-d-Gal-(1→3)-β-d-Gal-(1→4)-β-d-GlcNAcSEt involved in the hyperacute rejection response in xenotransplantation from pigs to man and as the specific receptor for toxin A from Clostridium difficile

  摘要：

  芽孢杆菌β-半乳糖苷酶的连续使用 环状菌和曲霉属的 α-半乳糖苷酶 米酵母产生线性 B 三糖 2，被鉴定为表位 在猪对人异种移植过程中结合抗 Gal 抗体 作为艰难梭菌毒素 A 的受体。

  DOI：

  10.1039/a607255k
• 作为产物：
  描述：

  乙基3,4,6-三-O-乙酰基-2-乙酰氨基-2-脱氧-beta-D-硫代吡喃葡萄糖苷 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 以100%的产率得到乙基2-乙酰氨基-2-脱氧-
  参考文献：
  名称：

  使用来自圆形芽孢杆菌的β-半乳糖苷酶化学酶促合成乙基1-硫基-（β-D-吡喃半乳糖基）-O - β -D-糖基葡糖基二糖

  摘要：

  已经使用环回芽孢杆菌的β-半乳糖苷酶作为生物催化剂，通过反式半乳糖基化反应合成了不同的乙基1-硫代-β-D-二糖。这种β-半乳糖苷酶在半乳糖基转移中主要表现出β-1–4特异性。GAL-β-（1-4）-O-β-d-GlcSEt 15以36％的产率得到，GAL-β-（1ndash; 4）-O-α-d-GlcSEt 19，收率30％，GAL- β-（1-4）-O-β-d-GalSEt 17在60％的产率，半乳糖-β-（1-4）-O-β-d-GalNAcSEt 20，49％收率，半乳糖-β-（1 -4）-O-β-d-Gal的-β-（1-4）-O-β-d-GalNAcSEt 21在9％的产率，半乳糖-β-（1-6）-O-β-d-GlcSEt 16在3％的产率和Gal-β-（1-3）-O-β-d-XylSEt 18在25％的产率。

  DOI：

  10.1016/0957-4166(96)00066-3

文献信息

• Syntheses of Modified Carbohydrates with Glycosidases: Stereo- and Regiospecific Syntheses of Lactosamine Derivatives and Related Compounds¹
  作者：Kurt G.I. Nilsson、Hefeng Pan、Ulla Larsson-Lorek

  DOI：10.1080/07328309708007328

  日期：1997.5

  Abstract Different lactosamine derivatives, modified in the 2-N- and anomeric positions and suitable as intermediates for synthesis of Lewis-x and related compounds, were prepared with high specificity on a multigram scale directly from lactose, employing different D-glucosamine derivatives as acceptors and the abundant β-D-galactosidase from Bullera singularis as catalyst. Thus, methyl O-β-D-gala

  摘要以不同的D-葡萄糖胺衍生物为接受剂，直接从乳糖以高克数级制备了在2-N-和端基异构体位置修饰，适合作为Lewis-x及相关化合物合成中间体的不同乳糖胺衍生物。并以奇异布拉氏菌中丰富的β-D-半乳糖苷酶为催化剂。因此，甲基O-β-D-吡喃半乳糖基-（1→4）-2-叠氮基-2-脱氧-β-D-吡喃葡萄糖苷，乙基O-β-D-吡喃半乳糖基-（1→4）-2-脱氧- 2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷和乙基O-β-D-吡喃半乳糖基-（1→4）-2-脱氧-2-（2,2,2-三氯乙氧基羰基氨基）-1-硫基-β -D-吡喃葡萄糖苷以基于添加的受体计算的20-40％的产率形成。不经色谱法（萃取/结晶步骤）分离出结晶形式的2-邻苯二甲酰亚胺基衍生物。三糖衍生物乙基O-β-D-吡喃半乳糖-（1→4）-O-β-D-吡喃半乳糖-（1→4）-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷也孤立。对应
• 401. The reaction of 2-acetamido-2-deoxy-D-glucose with ethanethiol and hydrochloric acid
  作者：L. Hough、Mahmoud I. Taha

  DOI：10.1039/jr9560002042

  日期：——
• 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
  作者：Katsuhiko Suzuki、Hironobu Hashimoto

  DOI：10.1016/s0008-6215(99)00253-0

  日期：1999.1

  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.
• Facile preparation of glycosyl donors for oligosaccharide synthesis: 2-azido-2-deoxyhexopyranosyl building blocks
  作者：Therese Buskas、Per J. Garegg、Peter Konradsson、Jean-Luc Maloisel

  DOI：10.1016/s0957-4166(00)86294-1

  日期：1994.11

  Facile routes to the 2-azido-2-deoxy-1-thioglycosides 6, 7, 15, and 18 and of the 2-azido-2-deoxy-4-pentenoglycoside 11, are described. These are useful intermediates for the synthesis of oligo-saccharides containing alpha-D-2-amino-2-deoxy (or 2-acetamido-2-deoxy) hexosyl residues in the galacto-, gluco-, and manno- series.
• Chemoenzymatic synthesis of ethyl 1-thio-(β-D-galactopyranosyl)-O-β-D-glycopyranosyl disaccharides using the β-galactosidase from Bacillus circulans
  作者：Gabin Vic、Jeremy J. Hastings、Oliver W. Howarth、David H.G. Crout

  DOI：10.1016/0957-4166(96)00066-3

  日期：1996.3

  Different ethyl 1-thio-β-D-disaccharides have been synthesised by transgalactosylation using the β-galactosidase from Bacillus circulans as biocatalyst. This β-galactosidase shows mainly a β-1–4 specificity in the galactosyl transfer. Gal-β-(1–4)-O-β-D-GlcSEt 15 was obtained in 36% yield, Gal-β-(1ndash;4)-O-α-D-GlcSEt 19 in 30% yield, Gal-β-(1–4)-O-β-D-GalSEt 17 in 60% yield, Gal-β-(1–4)-O-β-D-GalNAcSEt

  已经使用环回芽孢杆菌的β-半乳糖苷酶作为生物催化剂，通过反式半乳糖基化反应合成了不同的乙基1-硫代-β-D-二糖。这种β-半乳糖苷酶在半乳糖基转移中主要表现出β-1–4特异性。GAL-β-（1-4）-O-β-d-GlcSEt 15以36％的产率得到，GAL-β-（1ndash; 4）-O-α-d-GlcSEt 19，收率30％，GAL- β-（1-4）-O-β-d-GalSEt 17在60％的产率，半乳糖-β-（1-4）-O-β-d-GalNAcSEt 20，49％收率，半乳糖-β-（1 -4）-O-β-d-Gal的-β-（1-4）-O-β-d-GalNAcSEt 21在9％的产率，半乳糖-β-（1-6）-O-β-d-GlcSEt 16在3％的产率和Gal-β-（1-3）-O-β-d-XylSEt 18在25％的产率。