methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside | 72075-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside
• 英文别名: (2R,3S,4R,6S)-4-azido-6-methoxy-2-methyloxan-3-ol
• CAS: 72075-74-2
• 化学式: C₇H₁₃N₃O₃
• 分子量: 187.199
• InChiKey: MCEQCNCTLXUNDM-MVIOUDGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside 生成 (2R,3R,4R,6S)-4-Azido-6-methoxy-2-methyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  3-Azido-4-C-cyano-2,3,4,6-tetradeoxy-d-arabino-hexose trimethylene dithio-acetal, a d-glucose-derived, “chiral template” for the total synthesis of thienamycin

  摘要：

  DOI：

  10.1016/s0008-6215(00)81063-0
• 作为产物：
  描述：

  (2R,3S,4R,6S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol 在 吡啶 、 sodium hydroxide 、 sodium azide 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 192.0h， 生成 methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  3-Azido-4-C-cyano-2,3,4,6-tetradeoxy-d-arabino-hexose trimethylene dithio-acetal, a d-glucose-derived, “chiral template” for the total synthesis of thienamycin

  摘要：

  DOI：

  10.1016/s0008-6215(00)81063-0

文献信息

• Efficient Bis-C-Aminoglycosylation toward the Synthesis of the Pluramycins
  作者：Keisuke Suzuki、Takashi Matsumoto、Masayuki Shigeta、Tomohiko Hakamata、Yukie Watanabe、Kei Kitamura、Yoshio Ando

  DOI：10.1055/s-0030-1258766

  日期：2010.10

  Two bis-C-aminoglycosyl arenes containing the angolosamine and the vancosamine moieties, which are potentially useful as the D-ring fragments of the pluramycin-type antibiotics, were efficiently synthesized by the O→C-glycoside rearrangement based strategy.

  含有角洛糖胺和万古糖胺结构单元的两个双-C-氨基糖苷芳烃，它们作为多粘菌素类抗生素D环片段的潜在应用价值，通过O→C-糖苷重排策略高效合成。
• The total, stereocontrolled synthesis of a chemical precursor to (+)-thienamycin. A formal synthesis of the antibiotic
  作者：Stephen Hanessian、Denis Desilets、Georges Rancourt、Rejean Fortin

  DOI：10.1139/v82-327

  日期：1982.9.1

  A total synthesis of a key lactone intermediate in the synthesis of (+)-thienamycin is described, based on a strategy that uses "chiral templates" derived from D-glucose.

  基于使用衍生自 D-葡萄糖的“手性模板”的策略，描述了 (+)-硫霉素合成中关键内酯中间体的全合成。
• Synthèse de disaccharides polydésoxygénés et iodés
  作者：Belgacem Abbaci、Jean-Claude Florent、Claude Monneret

  DOI：10.1016/s0008-6215(00)90558-5

  日期：1992.4

  3-Amino-polydeoxy disaccharides have been prepared by condensation of a glycal with methyl 2,3,6-trideoxy-alpha-L-erythro- (or threo)-hex-2-enopyranoside in the presence of N-iodosuccinimide. After acid hydrolysis of the glycoside, 1,4-addition of hydrazoic acid to the corresponding hex-2-enopyranose led to 3-azido-disaccharides which were acetylated. Reduction of the azido group gave 2,2'-dideoxy- or 2,2'-dideoxy-2'-iodo compounds. Condensation of O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-1-O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranose with daunomycinone, followed by 3',4'-O-deacetylation produced the new anthracycline, 7-O-[O-(2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranosyl]-daunomycinone.
• Alternative preparation of methyl 3-amino-2,3,6-trideoxy-α-d-arabino-hexopyranoside and chiral intermediates for the synthesis of thienamycin
  作者：Andrew O. Stewart、Robert M. Williams

  DOI：10.1016/0008-6215(84)85014-4

  日期：1984.12
• Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents
  作者：Kazunobu Toshima、Tomonori Kimura、Ryusuke Takano、Tomohiro Ozawa、Akiko Ariga、Yutaka Shima、Kazuo Umezawa、Shuichi Matsumura

  DOI：10.1016/s0040-4020(03)00820-2

  日期：2003.8

  The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5' side guanine of the 5'-GG-3' site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.