methyl-3,4-di-O-acetyl-2,6-didesoxy-α-L-arabino-hexopyranoside | 72062-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-3,4-di-O-acetyl-2,6-didesoxy-α-L-arabino-hexopyranoside
• 英文别名: Methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexapyranoside；methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranoside；methyl 3,4-di-O-acetyl-2,6-dideoxy-L-arabino-hexopyranoside；[(2S,3S,4S,6R)-3-acetyloxy-6-methoxy-2-methyloxan-4-yl] acetate
• CAS: 72062-85-2
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: YYOUDJJKCIBTNG-HTCUVTCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl-3,4-di-O-acetyl-2,6-didesoxy-α-L-arabino-hexopyranoside 在 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside
  参考文献：
  名称：

  10.1002/asia.200900640.

  摘要：

  DOI：

  10.1002/asia.200900640.
• 作为产物：
  描述：

  methyl 3,4-di-O-acetyl-2-bromo-2,6-dideoxy-α-L-glucopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以81%的产率得到methyl-3,4-di-O-acetyl-2,6-didesoxy-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane

  摘要：

  The stereochemistry of dehalogenation of 2-halo sugars with tributyltin hydride has been investigated in terms of the influence of steric and conformational effects using deuterium-labeling techniques. Detailed analysis of the results (Tables I-III) demonstrates that the size and orientation of the ring substituents are a determining factor in the stereochemical outcome of the reaction' However, some results can only be explained considering reduction of two equilibrating radical conformers.

  DOI：

  10.1021/jo00059a037

文献信息

• Synthèse et réactivité vis-à-vis de réactifs nucléophiles des méthyl-3,4-anhydro-2,6-didésoxy-α- et -β-l-lyxo- et -ribo-hexopyranosides
  作者：Alain Martin、Mary Païs、Claude Monneret

  DOI：10.1016/0008-6215(83)88235-4

  日期：1983.3

  Abstract The ring-opening reactions of methyl 3,4-anhydro-2,6-dideoxy-α- and -β- l - lyxo - and - ribo -hexopyranosides with sodium azide, ammonia, methyl- and dimethylamine, and sodium methoxide were studied. Regioselectivity is explained in terms of steric and conformational factors.

  摘要3,4-脱水-2,6-二脱氧-α-和-β-l-lyxo-和-ribo-hexopyranosides甲基与叠氮化钠，氨水，甲基和二甲基胺以及甲醇钠的开环反应分别为研究过。区域选择性是根据空间和构象因素来解释的。
• Iodoalkoxylation of 1,5-anhydro-2-deoxy-hex-1-enitols (glycals)
  作者：Derek Horton、Waldemar Priebe、Marcos Sznaidman

  DOI：10.1016/0008-6215(90)80129-q

  日期：1990.9

  Exclusive trans-addition is observed in the iodoalkoxylation of the 6-membered cyclic enol ethers 3,4-di-O-acetyl-L-rhamnal (1), 3,4-di-O-acetyl-L-fucal (2), and related glycal derivatives. The main products from 1 and from 3,4,6-tri-O-acetyl-D-glucal (3) thus had the alpha-manno configuration. Similarly, alpha-talo products were obtained from 2 in 87-93% yield. The product distribution is not affected by the electronegativity of the 5-substituent. It is concluded that steric factors in the glycal and the nucleophile affect only the step of trans-diaxial opening of the intermediate iodonium ion. Enhanced yields of the desired trans-diaxial products were observed in reactions of glycals having the lyxo configuration when the reactions were conducted in tetrahydrofuran or methanol.
• Visible Light Mediated Activation and <i>O-</i>Glycosylation of Thioglycosides
  作者：Walter J. Wever、Maris A. Cinelli、Albert A. Bowers

  DOI：10.1021/ol302941q

  日期：2013.1.4

  Visible light catalysis allows the efficient construction of single electron transfer (SET) redox cycles that result in minimal formation of byproducts and proceed under exogenous control of a removable light source. The O-glycosylation of thioglycosides via visible light photoredox chemistry is reported. Mechanistic studies show that the reaction is fully light responsive and support a mechanism involving decomposition of an oxidatively generated sulfur radical cation and propagation via reduction of the thiol side product.
• Brimacombe, John S.; Hanna, Roderick; Saeed, May S., Journal of the Chemical Society. Perkin transactions I, 1982, # 11, p. 2583 - 2588
  作者：Brimacombe, John S.、Hanna, Roderick、Saeed, May S.、Tucker, Leslie C. N.

  DOI：——

  日期：——
• HORTON, DEREK;PRIEBE, WALDEMAR;SZNAIDMAN, MARCOS, CARBOHYDR. RES., 205,(1990) C. 71-86
  作者：HORTON, DEREK、PRIEBE, WALDEMAR、SZNAIDMAN, MARCOS

  DOI：——

  日期：——