methyl 2-deoxy-β-D-erythro-pentopyranoside | 17676-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-β-D-erythro-pentopyranoside
• 英文别名: methyl 2-deox-β-D-erythro-pentopyranoside；2-deoxy-α-(D)-ribopyranoside；methyl 2-deoxy-β-D-arabinopyranoside；methyl 2-deoxy-β-D-ribopyranoside；Me-β-D-ery-dPenp；methyl-(β-D-erythro-2-deoxy-pentopyranoside)；Methyl 2-deoxy-b-D-ribopyranoside；(3R,4S,6R)-6-methoxyoxane-3,4-diol
• CAS: 17676-20-9
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: CYLGOSOYSUHPCY-KVQBGUIXSA-N

物化性质

• 熔点：
  95 °C
• 沸点：
  112 °C(Press: 0.02 Torr)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-β-D-erythro-pentopyranoside 在 吡啶 、 sodium azide 、 potassium carbonate 、 对甲苯磺酰氯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-[(1R,4R,6R)-4-甲氧基-3-氧杂-7-氮杂双环[4.1.0]庚-7-基]乙酮
  参考文献：
  名称：

  加利车霉素的氨基糖成分（E环）的一个有效的立体选择性合成γ 1我

  摘要：

  一种简单，高效，立体选择性的甲基2,4-二脱氧-4-（乙基氨基）-3 - O-甲基-β-L-苏-戊吡喃糖苷2的合成，对应于E的单糖单元（E环）描述了加利车霉素1。合成程序利用甲基2-脱氧-β-D-核糖吡喃糖苷3作为对映体纯原料，并通过中间体活化的氮丙啶12的酸甲醇分解，分6步得到所需的氨基糖2，令人满意的高总收率（60％ ）。在合成过程的任何时候都不需要分离阶段。

  DOI：

  10.1016/0957-4166(96)00074-2
• 作为产物：
  描述：

  甲基 2,3-脱水-beta-D-核吡喃糖苷 在 甲醇 、 氢溴酸 、 镍 、 丙酮 作用下， 生成 methyl 2-deoxy-β-D-erythro-pentopyranoside
  参考文献：
  名称：

  Kent et al., Journal of the Chemical Society, 1949, p. 1232,1234

  摘要：

  DOI：

文献信息

• Stereochemical studies on esperamicins: Determination of the absolute configuration of isopropylamino sugar moiety
  作者：J. Golik、H. Wong、D.M. Vyas、T.W. Doyle

  DOI：10.1016/s0040-4039(01)80434-2

  日期：1989.1

  The absolute stereochmistry of the isopropylamino sugar moiety of esperamicin A1 was determined as the -pentopyranosyl by comparing the CD spectra of derivatized methanolysis product with those of two synthesized antipodal glycosides and .

  通过比较衍生的甲醇分解产物的CD光谱与两种合成的对映糖苷和的CD光谱，确定了埃斯帕米霉素A 1异丙基氨基糖部分的绝对立体化学为-戊吡喃糖基。
• Improved stereoselective synthesis of both methyl α- and β-glycosides corresponding to the amino sugar component of the E Ring of calicheamicin γ1I and esperamicin A1
  作者：Fabrizio Badalassi、Paolo Crotti、Lucilla Favero、Franco Macchia、Mauro Pineschi

  DOI：10.1016/s0040-4020(97)00921-6

  日期：1997.10

  monosaccharide component (α and β-anomer) of the E Ring of calicheamicin γ1I and esperamicin A1 has been synthetized by an efficient and improved stereoselective procedure starting from methyl 2-deoxy-α- and β-D-ribopyranoside. The synthetic procedure makes use, in each case, of a cyclic sulphate and of the regioselective ring opening of an intermediate activated aziridine.

  的E环的单糖组分（α和β端基异构体）刺孢霉素γ 1我和埃斯波霉素阿1已经通过从甲基2-脱氧- α-和β-d-ribopyranoside开始的有效和改进的立体选择性方法合成。在每种情况下，合成方法都使用环状硫酸盐和中间体活化的氮丙啶的区域选择性开环。
• An efficient stereoconvergent synthesis of the 4-ethylamino-2,4-dideoxy-l-threo-pentopyranose component of the calicheamicins and esperamicins
  作者：Eugene A. Mash、Sandeep K. Nimkar

  DOI：10.1016/0040-4039(93)85082-8

  日期：1993.1

  A stereconvergent synthesis of the 4-ethylamino-2,4-dideoxy-L-threo-pentopyranose coonponent of calicheamicins γ1, γ1I, α2I, and esperamicin A1b from methyl 2-deoxy-β-D-ribopyranoside is described. The synthesis requires eight steps in each branch. The overall yield is 54%. This synthesis should be adaptable for syntheses of the corresponding 4-methylamino)-2,4-dideoxy- L-threo- and 4-isopropylamino-2

  的stereconvergent合成4-乙基氨基-2,4-二脱氧L-苏-pentopyranose coonponent刺孢霉素γ的1，γ 1我，α 2予，和埃斯波甲1b中由2-脱氧- β-d-ribopyranoside是描述。该综合在每个分支中需要八个步骤。总产率为54％。该合成应适合于合成其他加利车霉素和艾司帕米霉素抗生素的相应的4-甲基氨基）-2,4-二脱氧-L-苏-和4-异丙基氨基-2.4-双脱氧-L-苏-戊糖成分。
• Overend et al., Journal of the Chemical Society, 1951, p. 992
  作者：Overend et al.

  DOI：——

  日期：——
• 3-Hydroxyleukotriene B4 (3-OH-LTB4): Total Synthesis and Stereochemical Assignment.
  作者：Rama K. Bhatt、Kamlesh Chauhan、Pat Wheelan、J. R. Falck、Robert C. Murphy

  DOI：10.1021/ja00091a004

  日期：1994.6

  The asymmetric total synthesis of 3-hydroxyleukotriene B-4 (3-OH-LTB(4)), an ethanol-inducible proinflammatory autacoid, was achieved using a triply convergent strategy for the sequential union of propargylic arsonium salt 3 with pyranosides 2a,b and furanose 4. Both saccharide subunits were derived from commercial 2-deoxy-D-ribose. The key transformation involved palladium-mediated coupling of bromoacetylenide 9 with stannylglycal 6a,b. Subsequent Rieke zinc hydrogenation of acetylene 10a,b and controlled ionic reduction of the cross-conjugated cyclic enol ether using NaBH3CN at pH similar to 4-4.5 established the cis-Delta(6,7)-olefin and C(5)-hydroxyl stereochemistry, respectively, and led to 11a,b. Methyllactol hydrolysis, PCC oxidation, methanolysis, and desilylation afforded 3(R)- and 3(S)-OH-LTB(4) methyl esters, respectively. On the basis of chromatographic and mass spectral comparisons, enzymatically derived 3-OH-LTB(4) is composed principally of the 3(S)-isomer (>95%).