methyl 2,3,4-trideoxy-α-D-glycero-hexopyranoside | 63358-56-5

• 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 2,3,4-trideoxy-α-D-glycero-hexopyranoside
• 英文别名: (2S,6S)-2-hydroxymethyl-6-methoxytetrahydropyran；[(2S,6S)-6-methoxyoxan-2-yl]methanol
• CAS: 63358-56-5
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: OAOIOIJKDGYSEQ-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-trideoxy-α-D-glycero-hexopyranoside 、 3,5-二硝基苯甲酰氯 以57%的产率得到[(2S,6S)-6-methoxyoxan-2-yl]methyl 3,5-dinitrobenzoate
  参考文献：
  名称：

  由d-葡萄糖基-1,5-内酯合成一些三脱氧-d-己糖及其衍生物

  摘要：

  摘要甲基2,3,4-丁氧基-α-d-和-β-d-甘油己吡喃糖苷（10和11）甲基α-d-和β-d-乙酰吡喃糖苷（24和25），（2S描述了）-1,2-己二醇（36），（2S）-1,1,2,6-己三醇（37），以及它们的一些衍生自d-葡萄糖基-1,5-内酯的衍生物。

  DOI：

  10.1016/0008-6215(92)84152-i
• 作为产物：
  描述：

  methyl 4-bromo-5,6-O-isopropylidene-2,3,4-trideoxy-D-threo-hexonate 在 盐酸 、 diisobutylaluminum hydride 、 氢气 、 sodium acetate 作用下， 以 甲醇 、 甲苯 、 Petroleum ether 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 methyl 2,3,4-trideoxy-α-D-glycero-hexopyranoside
  参考文献：
  名称：

  由d-葡萄糖基-1,5-内酯合成一些三脱氧-d-己糖及其衍生物

  摘要：

  摘要甲基2,3,4-丁氧基-α-d-和-β-d-甘油己吡喃糖苷（10和11）甲基α-d-和β-d-乙酰吡喃糖苷（24和25），（2S描述了）-1,2-己二醇（36），（2S）-1,1,2,6-己三醇（37），以及它们的一些衍生自d-葡萄糖基-1,5-内酯的衍生物。

  DOI：

  10.1016/0008-6215(92)84152-i

文献信息

• The high-pressure [4+2]cycloaddition of 1-methoxybuta-1,3-diene to the glycolaldehyde-derived heterodienophiles, catalyzed by chiral metallosalen complexes
  作者：Piotr Kwiatkowski、Wojciech Chaładaj、Małgorzata Malinowska、Monika Asztemborska、Janusz Jurczak

  DOI：10.1016/j.tetasy.2005.07.031

  日期：2005.9

  A high-pressure (ca. 10 kbar) reaction of 1-methoxybuta-1,3-diene 1 with variously O-protected glycolaldehydes 2, catalyzed by the chiral (salen)Cr(III)Cl 4a–d and 5 or (salen)Co(II) 6a–f and 7 complexes, has been studied. The best results were obtained for tert-butyldimethylsilyloxyacetaldehyde 2a. The reaction afforded, in good yield (up to 90%) and with very good diastereoselectivity (up to 92%)

  手性（salen）Cr（III）Cl 4a – d和5或（salen ）催化的1-甲氧基丁1,3-二烯1与各种O保护的乙醇醛2的高压（大约10 kbar）反应）Co（II）6a – f和7种配合物已被研究。叔丁基二甲基甲硅烷基氧基乙醛2a获得了最佳结果。该反应以[4 + 2]环加合物3a的高收率（最高90％）和非对映选择性（最高92％）和对映选择性（最高93％ee）提供。，是具有重大合成意义的化合物。讨论了环加成反应的立体化学模型。
• The enantioselective high-pressure Diels–Alder reaction of 1-methoxybuta-1,3-diene with tert-butyldimethylsilyloxyacetaldehyde catalyzed by (salen)Co(II) and (salen)Cr(III)Cl complexes
  作者：Małgorzata Malinowska、Piotr Kwiatkowski、Janusz Jurczak

  DOI：10.1016/j.tetlet.2004.08.081

  日期：2004.10

  reaction of 1-methoxybuta-1,3-diene (1) with tert-butyldimethylsilyloxyacetaldehyde (2), catalyzed by the chiral (salen)Co(II) 4 or (salen)Cr(III)Cl 5 complexes, has been studied. We found that the reaction afforded, in good yield (up to 90%) and both with very good diastereoselectivity (up to 92%) and enantioselectivity (up to 94% ee), the [4 + 2]cycloadducts 3, which are compounds of significant synthetic

  1-methoxybuta -1,3-二烯（的高压（10-11千巴）反应1）与叔-butyldimethylsilyloxyacetaldehyde（2）中，由催化手性（沙仑）钴（II）4或（沙仑）铬（ III）Cl 5配合物，已经被研究。我们发现该反应提供了[4 + 2]环加合物3，该化合物收率好（达90％），非对映选择性（达92％）和对映选择性（达94％ee）都很好。具有重要的综合意义。
• Stereochemistry of diels-alder reaction at high-pressure: influence of pressure on asymmetric induction in (4+2)cycloaddition of 1-methoxybuta-1,3-diene to 2,3-o-isopropylidene-D-glyceraldehyde
  作者：Janusz Jurczak、Tomasz Bauer

  DOI：10.1016/s0040-4020(01)88056-x

  日期：1986.1

  High-pressure (4+2)cycloaddition of 1-methoxybuta-1,3-diene ( to 2,3-O-isopropylidene-D-glyceraldehyde () afforded four diastereoisomeric 6-substituted 2-methoxy-5,6-dihydro-2H-pyrans (), for which the diastereoisomeric excess and absolute configuration were determined. The effects of pressure, temperature and solvent on asymmetric induction were examined. Stereochemical models were used for interpretation

  将1-甲氧基丁1,3-二烯（与2,3-O-异亚丙基-D-甘油醛（）进行高压（4 + 2）环加成反应，得到四个非对映异构体6-取代的2-甲氧基-5,6-二氢-确定了2H-吡喃（）的对映异构体过量和绝对构型，研究了压力，温度和溶剂对不对称诱导的影响，并使用立体化学模型解释了结果。
• Asymmetric induction in the high-pressure cycloaddition of 2,3-O-isopropylidene-D-glyceraldehyde to 1-methoxybuta-1,3-diene
  作者：Janusz Jurczak、Tomasz Bauer、Stanislaw Filipek、Marek Tkacz、Krystyna Zygo

  DOI：10.1039/c39830000540

  日期：——

  The high-pressure cycloaddition of 2,3-O-isopropylidene-D-glyceraldehyde (7) to 1-methoxybuta-1,3-diene (1) afforded the diastereoisomeric cycloadducts (3) for which the diastereoisomeric excess and absolute configuration have been determined.

  2,3-的高压环加成ö异亚丙基d甘油醛（7）至1-methoxybuta -1,3-二烯（1），得到非对映异构cycloadducts（3为其非对映异构过量和绝对构型已经）决心。
• Carbon-13 NMR spectra of saturated heterocycles: XI—Tetrahydropyrans (oxanes)
  作者：Ernest L. Eliel、Muthiah Manoharan、K. Michal Pietrusiewicz、Karl D. Hargrave

  DOI：10.1002/omr.1270210205

  日期：1983.2

  AbstractThe 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without methyl substituents at various ring positions, some of them bearing in addition (or instead) ethyl, vinyl, ethynyl, carbomethoxy and methylol substituents at C‐2, have been recorded, and the 294 resulting chemical shifts have been correlated by multiple linear regression analysis. Axial and equatorial α‐, β‐, γ‐, δ‐, gem‐ and vic‐parameters for shifts caused by methyl groups at all ring positions, and similar parameters for Et,—CHCH2,—CCH, CO2Me and CH2OH groups at C‐2, are reported. Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and experimental shifts is excellent. This is probably the largest parameter set of this type extant. 13C NMR spectra of a number of additional substituted tetrahydropyrans, and of 3,6‐dihydro‐2H‐pyrans and 3,4‐dihydro‐2H‐pyrans, are tabulated and discussed.