(2R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-one | 40246-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-one
• CAS: 40246-34-2
• 化学式: C₃₉H₄₆O₁₁
• 分子量: 690.788
• InChiKey: GXYUWYSMPRLSLR-LHIXTURWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-one 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Route from Glycals to Mannose .beta.-Glycosides

  摘要：

  DOI：

  10.1021/jo00086a047
• 作为产物：
  描述：

  3,4,6-Tri-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-diisopropylidene-α-D-galactopyranoside 在 乙酸酐 、 二甲基亚砜 作用下， 反应 48.0h， 生成 (2R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-one
  参考文献：
  名称：

  Route from Glycals to Mannose .beta.-Glycosides

  摘要：

  DOI：

  10.1021/jo00086a047

文献信息

• Stereospecific Access to β-Mannosides from Glucose-derived 1,2-Orthoesters as Glycosyl Donors
  作者：Eisuke Kaji、Yugo Hosokawa、Yusuke Watanabe、Mina Kobayashi、Mayumi Yamakawa

  DOI：10.3987/com-03-s60

  日期：——

  A new, stereospecific synthesis of beta-mannosides from glucose-derived 1,2-orthoesters has been developed by a simple four step procedure, comprising beta-specific glycosidation of the 1,2-orthoesters, 2'-O-deacetylation, 2'-O-triflation, and SN 2 type inversion of the triflyl group providing beta-D-Man-(1-->6)-D-Gal, and beta-D-Man-(1-->4)-D-Glc derivatives in reasonable yield.
• 3,4,6-Tri-O-benzyl-.alpha.-D-arabino-hexopyranos-2-ulosyl Bromide: A Versatile Glycosyl Donor for the Efficient Generation of .beta.-D-Mannopyranosidic Linkages
  作者：Frieder W. Lichtenthaler、Thomas Schneider-Adams

  DOI：10.1021/jo00101a035

  日期：1994.11

  An expedient four-step sequence is described for the conversion of acetobromoglucose into the title 2-oxohexosyl (''ulosyl'') bromide 4. Due to its O-benzyl protection, 4 is considerably more reactive than its acylated analogs 1-3: Ag2CO3-promoted glycosidations with 2-propanol, diacetone-galactose, and methyl 2,3-O-isopropylidene-alpha-L-rhamnoside are complete within minutes and, in addition, are endowed with beta-specificity. This renders ulosyl bromide 4 a most propitious, indirect beta-D-mannosyl donor, inasmuch as the borohydride reduction of the beta-D-glycosiduloses formed (14-16 --> 19, 21, and 22) proceeds with manno selectivities of >20:1. Comparative evaluation of the manno/gluco ratios obtained in all 21 beta-D-arabino hexosidulose reductions (Table 1) reveals the 3-O-blocking group to have a pronounced effect on the outcome: >20:1 in cases with a 3-O-benzyl group versus only 2:1 to 3:1 in the presence of 3-O-acyl functions.