Methyl 4-(N-acetyl)ethylamino-3-O-methyl-2,4-deoxy-α-L-threo-pentopyranoside | 108212-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Methyl 4-(N-acetyl)ethylamino-3-O-methyl-2,4-deoxy-α-L-threo-pentopyranoside
• 英文别名: Methyl 2,4-dideoxy-4-(N-ethylacetamido)-3-O-methyl-α-L-threo-pentopyranoside；N-[(3S,4S,6R)-4,6-dimethoxyoxan-3-yl]-N-ethylacetamide
• CAS: 108212-85-7
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: OEELCJHZFBCGKL-GARJFASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2,4-dideoxy-3-O-methyl-4-(N-acetylamino)-α-L-xylopyranoside 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 Methyl 4-(N-acetyl)ethylamino-3-O-methyl-2,4-deoxy-α-L-threo-pentopyranoside
  参考文献：
  名称：

  calicheamicins和esperamicins的4-乙基氨基-2,4-二脱氧-1-苏-戊吡喃糖成分的高效立体收敛合成

  摘要：

  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。

  DOI：

  10.1016/0040-4039(93)85082-8

文献信息

• Preparation of the 4-ethylamino sugar of calicheamicin: Assignment of absolute configuration.
  作者：Daniel Kahne、Dan Yang、May D Lee

  DOI：10.1016/s0040-4039(00)94323-5

  日期：1990.1

  The absolute configuration of the 4-ethylamino sugar of calicheamicin is established to be 3S,4S by comparison with material obtained from asymmetric synthesis from L-serine.

  与从L-丝氨酸的不对称合成获得的材料相比，加利车霉素的4-乙基氨基糖的绝对构型被确定为3S，4S。
• 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。
• Asymmetric Allylboration of 2-N,3-O-Isopropylidene-N-Boc-L-serinal: Diastereoselective Synthesis of the Calicheamicin .gamma.1I Amino Sugar
  作者：William R. Roush、J. A. Hunt

  DOI：10.1021/jo00109a008

  日期：1995.2

  Syntheses of the calicheamicin amino sugar 6 and its erythro diastereomer 7 have been completed by a sequence involving the asymmetric allylboration of N-Boc-serinal acetonide L-8 with the tartrate ester modified allylboronates (R,R)-9 and (S,S)-9, respectively. The reaction of(R,R)-9 and L-8 in toluene provides 14 with 89:11 selectivity, whereas the reaction of(S,S)-9 with L-8 in Et(2)O provides the diastereomer 15 with 90:10 selectivity. It is shown that the relatively modest diastereoselectivity of these double asymmetric reactions is compromised by the low enantiomeric purity of 8 (86-87% ee), and data are provided indicating that these reactions should be highly diastereoselective (greater than or equal to 95:5 in each case) if performed with enantiomerically pure aldehyde. The two diastereomeric homoallylic alcohols, 14 and 15, are easily elaborated into the targeted amino sugars 6 and 7 via the acetamide-substituted pyranosides 22 and 26. Methyl pyranosides 22a and 22e were shown to adopt preferentially the unexpected conformations B and D, with axial acetamide substituents, in nonpolar solvents, while the expected conformations A and C were strongly favored in d(6)-DMSO because of hydrogen bonding interactions with the solvent. The syntheses of 6 and 7 reported herein are expected to facilitate the design and synthesis of analogs of the calicheamicin aryl tetrasaccharide 3, which should prove useful in further analysis and applications of oligosaccharides as DNA binders.
• KAHNE, DANIEL;YANG, DAN;LEE, MAY D., TETRAHEDRON LETT., 31,(1990) N, C. 21-22
  作者：KAHNE, DANIEL、YANG, DAN、LEE, MAY D.

  DOI：——

  日期：——
• Mash, Eugene A.; Nimkar, Sandeep K.; DeMoss, Suzanne M., Journal of Carbohydrate Chemistry, 1995, vol. 14, # 9, p. 1369 - 1378
  作者：Mash, Eugene A.、Nimkar, Sandeep K.、DeMoss, Suzanne M.

  DOI：——

  日期：——