Methyl 4-azido-3-O-methyl-2,4-dideoxy-α-L-threo-pentopyranoside | 147860-17-1

• 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-azido-3-O-methyl-2,4-dideoxy-α-L-threo-pentopyranoside
• 英文别名: methyl 4-azido-2,4-dideoxy-3-O-methyl-α-L-threo-pentopyranoside；(2R,4S,5S)-5-azido-2,4-dimethoxyoxane
• CAS: 147860-17-1
• 化学式: C₇H₁₃N₃O₃
• 分子量: 187.199
• InChiKey: IWSQMDHSWKEOKV-LYFYHCNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-azido-3-O-methyl-2,4-dideoxy-α-L-threo-pentopyranoside 在 platinum(IV) oxide lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 为溶剂， 生成 methyl 2,4-dideoxy-4-(ethylamino)-3-O-methyl-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
• 作为产物：
  描述：

  Methanesulfonic acid (3R,4S,6R)-4,6-dimethoxy-tetrahydro-pyran-3-yl ester 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以95%的产率得到Methyl 4-azido-3-O-methyl-2,4-dideoxy-α-L-threo-pentopyranoside
  参考文献：
  名称：

  Studies Related to the Carbohydrate Sectors of Esperamicin and Calicheamicin: Definition of the Stability Limits of the Esperamicin Domain and Fashioning of a Glycosyl Donor from the Calicheamicin Domain

  摘要：

  The core trisaccharide regions of esperamicin and the aryltetrasaccharide region of calicheamicin have been synthesized. The minimum protection modalities necessary to stabilize structures against rearrangement to an isomeric azafuranose series were ascertained (see compounds 12 and 65). Deprotection of the 2-(trimethylsilyl)ethoxycarbonyl carbamate from 65 led to azafuranose 14 characterized as methyl glycoside 15. Using this insight, it was possible to fashion, for the first time, a pre-glycosyl donor (see compound 128) corresponding to the complete arylsaccharide sector of calicheamicin gamma(1)(I) at the oxidation level of the domain. Among the key assembly strategies were the conversion of alpha-thiophenylpseudoglycals to allal derivatives (see 44 --> 45); the interfacing of epoxide-mediated glycosylation with iodoglycosylation (see 30 --> 47 --> 48); the synthesis of hydroxylamine glycosides via triflate displacement (see 61 + 91 --> 101); and a new route to p-hydroxybenzonitriles (see formation of 86).

  DOI：

  10.1021/ja00126a013

文献信息

• 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：——
• Studies Related to the Carbohydrate Sectors of Esperamicin and Calicheamicin: Definition of the Stability Limits of the Esperamicin Domain and Fashioning of a Glycosyl Donor from the Calicheamicin Domain
  作者：Randall L. Halcomb、Serge H. Boyer、Mark D. Wittman、Steven H. Olson、Derek J. Denhart、Kevin K. C. Liu、Samuel J. Danishefsky

  DOI：10.1021/ja00126a013

  日期：1995.5

  The core trisaccharide regions of esperamicin and the aryltetrasaccharide region of calicheamicin have been synthesized. The minimum protection modalities necessary to stabilize structures against rearrangement to an isomeric azafuranose series were ascertained (see compounds 12 and 65). Deprotection of the 2-(trimethylsilyl)ethoxycarbonyl carbamate from 65 led to azafuranose 14 characterized as methyl glycoside 15. Using this insight, it was possible to fashion, for the first time, a pre-glycosyl donor (see compound 128) corresponding to the complete arylsaccharide sector of calicheamicin gamma(1)(I) at the oxidation level of the domain. Among the key assembly strategies were the conversion of alpha-thiophenylpseudoglycals to allal derivatives (see 44 --> 45); the interfacing of epoxide-mediated glycosylation with iodoglycosylation (see 30 --> 47 --> 48); the synthesis of hydroxylamine glycosides via triflate displacement (see 61 + 91 --> 101); and a new route to p-hydroxybenzonitriles (see formation of 86).
• 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。