methyl 2--2-deoxy-β-D-glucopyranoside | 4704-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2--2-deoxy-β-D-glucopyranoside
• 英文别名: methyl 2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside；benzyl ((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3-yl)carbamate；methyloside-2-benzyloxycarbonamido-2-deoxy-a-D-glucopyranose；β-Methyl-2-desoxy-2-carbobenzoxyamino-D-glucopyranosid；1-O-Methyl-N-benzyloxycarbonyl-β-D-glucosamin; 1-O-Methyl-2-(N-benzyloxycarbonyl)amino-2-desoxy-β-D-glucopyranose；(O¹-Methyl-β-D-glucopyranose-2-yl)-carbamidsaeure-benzylester；(O¹-methyl-β-D-glucopyranose-2-yl)-carbamic acid benzyl ester；Methyl-(2-benzyloxycarbonylamino-2-desoxy-β-D-glucopyranosid)；benzyl N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]carbamate
• CAS: 4704-17-0
• 化学式: C₁₅H₂₁NO₇
• 分子量: 327.334
• InChiKey: MXCBPGJIPRBQAE-DHGKCCLASA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  564.9±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2--2-deoxy-β-D-glucopyranoside 在 platinum on activated charcoal 氧气 作用下， 以 水 为溶剂， 反应 50.0h， 以54%的产率得到(2S,3S,4R,5R,6R)-3,4-dihydroxy-6-methoxy-5-(phenylmethoxycarbonylamino)oxane-2-carboxylic acid
  参考文献：
  名称：

  含糖氨基酸的线性和环状肽的合成和构象分析

  摘要：

  糖氨基酸 (SAA) 被设计和合成为新的非肽肽模拟物，利用碳水化合物作为肽构建块。它们代表带有氨基和羧基官能团的类糖环结构，并且由于它们在刚性吡喃糖环中的不同取代模式，因此对肽的骨架具有特定的构象影响。已经合成了五种不同的 SAA（SAA1α、SAA1β、SAA2、SAA3 和 SAA4），它们显示出限制线性骨架构象或不同转角结构的能力。涉及 SAA 的线性和环状肽已在溶液中以及通过固相合成制备。SAA1α 和 SAA2 被整合到两个线性亮氨酸-脑啡肽类似物中，取代了天然的 Gly-Gly 二肽。NMR 研究为碳水化合物部分的构象诱导作用提供了证据。SAA2 和 SAA3 已被置于生长抑素的环状六肽类似物中；SAA4 被掺入模型肽中。的构造...

  DOI：

  10.1021/ja961068a
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 碳酸氢钠 、 乙酰氯 作用下， 以 水 为溶剂， 反应 24.0h， 生成 methyl 2--2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Hybrid Aminoglycoside Antibiotics via Tsuji Palladium-Catalyzed Allylic Deoxygenation

  摘要：

  Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an alpha,beta-unsaturated 6'-aldehyde and an allylic 3'-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd-2(dba)(3) and Bu3P granted access to a novel series of 3',4'-dideoxy-4',5'-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

  DOI：

  10.1021/ol2027703

文献信息

• Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases
  作者：Duncan C. Miller、Benoit Carbain、Gary S. Beale、Sari F. Alhasan、Helen L. Reeves、Ulrich Baisch、David R. Newell、Bernard T. Golding、Roger J. Griffin

  DOI：10.1039/c5ob00211g

  日期：——

  An improved synthesis from d-glucosamine of a purported Sulf-2 inhibitor is described, with assay data for this compound and analogues showing only weak inhibition of Sulf-2, and sulfatases ARSA or ARSB.

  一种据称的Sulf-2抑制剂从D-葡萄糖胺中改进的合成方法被描述，该化合物及其类似物的测定数据显示对Sulf-2、磺酶ARSA或ARSB的抑制作用较弱。
• Stereospecific synthesis of methyl 2-amino-2-deoxy-(6S)-deuterio-α,β-d-glucopyranoside and methyl 2,6-diamino-2,6-dideoxy-(6R)-deuterio-α,β-d-glucopyranoside: Side chain conformations of the 2-amino-2-deoxy and 2,6-diamino-2,6-dideoxyglucopyranosides
  作者：Takayuki Kato、Andrea Vasella、David Crich

  DOI：10.1016/j.carres.2017.05.015

  日期：2017.8

  The stereospecifically labeled 6-monodeuterio methyl 2,6-diamino-2,6-dideoxy-α- and β- d-glucopyranosides were synthesized with a view to determining their side chain conformations. NMR studies in D2O at pH 5 and pH 11 reveal both anomers to adopt very predominantly the gt conformation consistent with the gauche conformation of 2-aminoethanol and its acetate salt. In contrast, as also revealed with

  为了确定它们的侧链构象，合成了立体定向标记的6-单十二烷基甲基2,6-二氨基-2,6-二脱氧-α-和β-d-吡喃葡萄糖苷。在pH 5和pH 11的D2O中进行的NMR研究表明，两种端基异构体都主要采用gt构象，该构象与2-氨基乙醇及其乙酸盐的gauche构象一致。相反，正如在立体定向标记的单氘异位异构体的帮助下所揭示的那样，甲基2-氨基-2-脱氧-α-和β-d-吡喃葡萄糖苷是大约1：1的gg和gt构象异构体混合物。吡喃葡萄糖本身。
• Verwendung von D-glucopyranuronsäuren und deren Derivate zum Einbau in pharmakologisch wirksame Peptide und deren Salze
  申请人：ASTA Medica Aktiengesellschaft

  公开号：EP0652225A1

  公开（公告）日：1995-05-10

  Verwendung von 7-Amino-L-glycero-L-gulo-2,6-anhydro-7-desoxy-heptonsäure und 2-Benzoxycarbonylamino-0¹-methyl-2-desoxy-β-glucopyranuronsäure, ihrer Derivate und der enantiomeren Verbindungen zum Einbau und zur Herstellung in pharmakologisch wirksame Peptidhormone.

  7-amino-L-glycero-L-gulo-2,6-anhydro-7-deoxy-heptonic acid 和 2-benzoxycarbonylamino-0¹-methyl-2-deoxy-β-glucopyranuronic acid、它们的衍生物和对映体化合物用于掺入和制备药理活性肽类激素。
• SYNTHESIS AND CONFORMATIONAL INVESTIGATIONS OF SULFATED CARBOHYDRATES1
  作者：Katrin Probst、Hans Wessel

  DOI：10.1081/car-100108273

  日期：——

  Starting from the finding that methyl 2,3,4,6-tetra-O-sulfonato-beta -D-glucopyranoside (3) existed in a conformational equilibrium of the two chair conformers, the effect of sulfation on conformational equilibria was further investigated using a number of sulfated saccharides. Three sulfate groups on positions 3,4, and 6 or two on positions 2 and 3 were not sufficient to induce the conformational change as shown with methyl 2-amino-2-deoxy-3,4,6-tri-O-sulfonato-beta -D-glucopyranoside. N-Sulfation of the amino group of the latter compound furnished an equilibrium of chair conformers with less (1)C(4) con-former content than for 3. The presence of persulfated methyl P-D-galactopyranoside in the usual (4)C(1) conformation suggested the involvement of the 4-O-sulfate in the effect. Methyl 2,3,4-tri-O-sulfonato-beta -D-xylopyranoside was found to prefer the "all-axial" (1)C(4) conformation demonstrating that O-sulfates facilitate 1,3-O/O-diaxial interactions better than ester groups and in particular benzoates. Also, sulfated 1,5-anhydro-D-glucitol occurred as a conformational mixture, the influence of the anomeric effect may thus have been overestimated in the previous discussion of this conformational effect.
• Foster et al., Journal of the Chemical Society, 1957, p. 81,85
  作者：Foster et al.

  DOI：——

  日期：——