methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside | 3868-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside
• 英文别名: methyl 3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranoside；Methyl-3-benzyl-O⁴-methyl-2,6-didesoxy-α-D-galactopyranosid>；Methyl-3-O-benzyl-2,6-didesoxy-4-O-methyl-α-D-lyxo-hexopyranosid；(2R,3S,4R,6S)-3,6-dimethoxy-2-methyl-4-phenylmethoxyoxane
• CAS: 3868-01-7
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: UMGPNXHDUWBRIX-RZFFKMDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside 在 palladium on activated charcoal 草酰氯 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.83h， 生成 methyl 3-C-cyano-2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranoside
  参考文献：
  名称：

  Syntheses of d-rubranitrose and methyl α-d-tetronitroside by cyanomesylation of hexopyranosid-3-uloses

  摘要：

  DOI：

  10.1016/s0008-6215(00)90152-6
• 作为产物：
  描述：

  methyl 6-deoxy-3,4-O-isopropylidene-2-O-<(methylthio)thiocarbonyl>-α-D-talopyranoside 在 盐酸 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 36.0h， 生成 methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside
  参考文献：
  名称：

  Kjoelberg, Ove; Neumann, Klaus, Acta Chemica Scandinavica, 1993, vol. 47, # 7, p. 721 - 727

  摘要：

  DOI：

文献信息

• Total synthesis of the AB disaccharide unit of olivomycin A
  作者：William R Roush、Julie A Straub

  DOI：10.1016/s0040-4039(00)84793-0

  日期：1986.1

  An efficient (10 step, 17% overall yield), highly diasteroselective total synthesis of disaccharide , corresponding to the AB disaccharide unit of olivomycin A, is described.

  描述了一种有效的（10步，总收率17％），高度非对映选择性的二糖全合成，对应于寡霉素A的AB二糖单元。
• A highly stereoselective synthesis of the AB disaccharide unit of olivomycin A
  作者：William R. Roush、Xiaofa Lin、Julie A. Straub

  DOI：10.1021/jo00004a054

  日期：1991.2

  A highly stereoselective synthesis of the AB disaccharide (4c) of olivomycin A is described. The synthesis features the double asymmetric allylboration of alpha,beta-dialkoxy aldehyde 8 using tartrate allylboronate (S,S)-9, which provides triol derivative 10 with the correct relative and absolute stereochemistry for utilization in syntheses of the A and B monosaccharides. The derived diol benzyl ether 11 was converted into 3-hydroxy-2-deoxy-lyxo-pyranoside 16 and thioglycoside 18 via the intermediacy of alpha-methyl 2-deoxy-lyxo-pyranoside 14-alpha, and then 16 and 18 were coupled in CH2Cl2 at 23-degrees-C by using Nicolaou's NBS thioglycosidation procedure to give the alpha,alpha-disaccharide 4a with > 6:1 selectivity. Difficulties encountered in the hydrolysis or activation of the methyl glycoside function of 4a prompted the synthesis to be revised by using intermediates containing more easily deprotected anomeric silyl (TBDMS) ethers. Diol 11 was thus selectivity monosilylated to give 21, which was smoothly converted via 2-deoxy-lyxo-pyranose 23 into thioglycoside 18 and 2-deoxypyranoside 27, which possesses a TBMDS protecting group at the anomeric center. Intermediates 18 and 27 were coupled again by using the Nicolaou methodology in a CH3CN-THF cosolvent mixture at -42-degrees-C to give the AB disaccharide TBDMS acetal 4b with greater-than-or-equal-to 20:1 selectivity. Deprotection of the anomeric TBDMS acetal by using Et3NH+F- in CH3CN then completed the synthesis of the olivomycin AB disaccharide unit 4c.
• GURJAR, M. K.;GHOSH, P. K., J. CARBOHYDR. CHEM., 7,(1988) N, C. 799-804
  作者：GURJAR, M. K.、GHOSH, P. K.

  DOI：——

  日期：——
• ROUSH, WILLIAM R.;LIN, XIAOFA;STRAUB, JULIE A., J. ORG. CHEM., 56,(1991) N, C. 1649-1655
  作者：ROUSH, WILLIAM R.、LIN, XIAOFA、STRAUB, JULIE A.

  DOI：——

  日期：——
• Syntheses of d-rubranitrose and methyl α-d-tetronitroside by cyanomesylation of hexopyranosid-3-uloses
  作者：Juji Yoshimura、Amjad Aqeel、Namgi Hong、Ken-Ichi Sato、Hironobu Hashimoto

  DOI：10.1016/s0008-6215(00)90152-6

  日期：1986.11