methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside | 34299-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside
• 英文别名: methyl 2-deoxy-2-(methoxycarbonyl)amino-α-D-glucopyranoside；methyl 2-deoxy-2-methoxycarbonylamino-α-D-glucopyranoside；Methyl-2-desoxy-2-methoxycarbonylamino-α-D-glucopyranosid
• CAS: 34299-66-6
• 化学式: C₉H₁₇NO₇
• 分子量: 251.236
• InChiKey: IFNPXEQMSNRYKA-PVFLNQBWSA-N

物化性质

• 沸点：
  473.4±45.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  117.48
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 乙醇 、 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Highly enantioselective diethylzinc addition to aldehydes catalyzed by d-glucosamine derivatives

  摘要：

  Synthesis of a-hydroxy sulfonamides derived from D-glucosamine and their application as ligands in the titanium tetraisopropoxide-promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aidehydes is presented. The reaction is highly enantioselective and enantiomeric excesses of up to 97% for benzaldehyde and 88% for n-hexanal were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00053-8
• 作为产物：
  描述：

  甲醇 、 D-glucosamine hydrochloride 、 氯甲酸甲酯 在 sodium 、 sodium carbonate 作用下， 以80%的产率得到methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient Syntheses of Methyl 2-Amino-2-Deoxy-3,4,6-Tri-O-Benzyl-α-D-Glucopyranoside and its 2-tert-Butoxycarbonylamino- and 2-Methylamino Derivatives fromN-Acetyl-D-Glucosamine

  摘要：

  The synthesis of the title compounds started with N-acetylglucosamine which was converted into the corresponding methyl glycoside and O-protected with benzyl groups. Subsequent N-protection as its N-BOC-N-acetyl derivative and sequential removal of the N-acetyl group and of the BOC group led in good yield to the target compounds in multigram amounts.

  DOI：

  10.1080/07328309908544030

文献信息

• Synthesis of (3<i>S</i>,4<i>S</i>)-Statine and a Related Compound, (3<i>S</i>,4<i>S</i>)-AHPPA, from D-Glucosamine as a Chiral Pool
  作者：Katsuo Shinozaki、Kazuhiro Mizuno、Hirohisa Oda、Yukio Masaki

  DOI：10.1246/bcsj.69.1737

  日期：1996.6

  4S)-statine ((3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid) (1) and (3S,4S)-AHPPA (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid) (2), were synthesized starting from D-glucosamine (3) as a chiral pool. Two routes for the transformation of D-glucosamine to key intermediates, which are applicable to the synthesis of threo-β-hydroxy-γ-amino acids, were investigated. The successful route involved

  生物学上重要的苏-β-羟基-γ-氨基酸，(3S,4S)-statine ((3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid) (1) 和 (3S,4S)- AHPPA (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid) (2) 从 D-葡糖胺 (3) 开始合成为手性池。研究了将 D-氨基葡萄糖转化为关键中间体的两条路线，适用于合成苏式-β-羟基-γ-氨基酸。成功的路线包括 C(6)-碳降解和 D-葡糖胺的 C(4)-羟基的消除，分 8 步，总产率为 30%，以提供 (4R,5S)-2-oxo-5-vinyloxazolidine- 4-甲醛二甲基乙缩醛 (17)，已被用作合成目标化合物的通用中间体。
• Reaction of methyl 2-deoxy-3-o-sulfonyl-2-p-toluenesulfonamido-α- and β-d-glucopyranoside derivatives with halide ions
  作者：Toshiaki Miyake、Tsutomu Tsuchiya、Yoshiaki Takahashi、Sumio Umezawa

  DOI：10.1016/s0008-6215(00)85251-9

  日期：1981.3

  Abstract Methyl 2-deoxy-3- O -sulfonyl-2- p -toluenesulfonamido-α- d -glucopyranoside derivatives were treated with halides in N , N -dimethylformamide. The corresponding 3-halo-α- d -glucopyranosides were formed by a double S N 2 process in high yields via the 3-halo-α- d -allopyranosides, despite the presence of an axial methoxyl group at C-1. The reactions proceeded more readily than the reaction for

  摘要在N，N-二甲基甲酰胺中用卤化物处理了2-脱氧-3-O-磺酰基-2-对甲苯磺酰胺基-α-d-吡喃葡萄糖苷衍生物。尽管在C-1处存在轴向甲氧基，但通过3-SN-α-d-吡喃吡喃糖苷通过双SN 2工艺以高收率形成了相应的3-卤-α-d-吡喃葡萄糖苷。该反应比进行甲基4，6-O-环己叉基-2-脱氧-3-O-对甲苯磺酰基-2-对甲苯磺酰胺基-β-d-吡喃葡萄糖苷的反应更容易进行。讨论了α-d端基异构体在C-3处准备位移的机理。在三丁基锡烷或液态氨中的钠的作用下，由相应的3-卤化物制得脱氧化合物。甲基4的处理
• Enantioselective addition of diethylzinc to aldehydes catalyzed by d-glucosamine derivatives: Highly pronounced effect of trifluoromethylsulfonamide
  作者：Tomasz Bauer、Sławomir Smoliński

  DOI：10.1016/j.apcata.2010.01.009

  日期：2010.3.1

  promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-trifluoromethylosulfonamido-d-glucosamine derivative is one of the most active ligands known and only 1 mol% of the ligand is sufficient for efficient catalysis of diethylzinc addition. The reaction is highly enantioselective for some aromatic aldehydes and enantiomeric excess up to 99%

  我们介绍了从d-氨基葡萄糖衍生的β-羟基磺酰胺的合成及其在四异丙醇钛中作为配体的应用，促进了二乙基锌与苯甲醛和选定的芳族和脂族醛的对映选择性加成。所述Ñ -trifluoromethylosulfonamido- d葡糖胺衍生物是已知的最活跃的配体之一，仅1摩尔％的所述配体的足够用于二乙基锌加入有效催化。该反应对于某些芳族醛是高度对映体选择性的，并且得到高达99％的对映体过量。
• Synthesis of D-erythro-Sphingosine from D-Glucosamine.
  作者：Katsuo SHINOZAKI、Kazuhiro MIZUNO、Yukio MASAKI

  DOI：10.1248/cpb.44.927

  日期：——

  D-erythro-Sphingosine (1) was synthesized from D-glucosamine (2) as a chiral pool through stereoinversion of the C(3)-hydroxyl group via an oxidation-reduction sequence, transformation to the erythro-amino-alcohol chiron (9) protected as the oxazolidinone, and elongation of the side chain at the C(6)-position of the derived chloride (12).

  D-赤型-鞘氨醇 (1) 由 D-葡萄糖胺 (2) 作为手性池，通过氧化还原序列对 C(3)-羟基进行立体反转，转化为赤型氨基醇 Chiron (9 ) 被保护为恶唑烷酮，并在衍生的氯化物 (12) 的 C(6)-位处延长侧链。
• Synthesis of the precursor of (+)-thienamycin utilizing D-glucosamine
  作者：Masaaki Miyashita、Noritaka Chida、Akira Yoshikohsi

  DOI：10.1039/c39820001354

  日期：——

  D-Glucosamine was transformed into the known synthetic intermediate (18) of (+)-thienamycin (1).

  D-葡萄糖胺被转化为（+）-噻吩霉素（1）的已知合成中间体（18）。