4,8-anhydro-2-C-methyl-5,6,7,9-tetra-O-benzyl-1,2,3-trideoxy-D-glycero-D-gulo-nonitol | 141197-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,8-anhydro-2-C-methyl-5,6,7,9-tetra-O-benzyl-1,2,3-trideoxy-D-glycero-D-gulo-nonitol
• 英文别名: α-1,5-anhydro-1-C-isobutyl-2,3,4,6-tetra-O-benzyl-D-glucitol；(2R,3S,4R,5R,6R)-2-(2-methylpropyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 141197-14-0
• 化学式: C₃₈H₄₄O₅
• 分子量: 580.764
• InChiKey: CIALZTIICVKKPR-JTDOPDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 、 三异丁基铝 生成 4,8-anhydro-2-C-methyl-5,6,7,9-tetra-O-benzyl-1,2,3-trideoxy-D-glycero-D-gulo-nonitol
  参考文献：
  名称：

  TOLSTIKOV, G. A.;PROXOROVA, N. A.;SPIVAK, A. YU., 5 BCEC. KONF. PO METALLOORGAN. XIMII, YURMALA, 1-4 APR., 1991: TEZ. DOKL.+

  摘要：

  DOI：

文献信息

• Tolstikov, G. A.; Prokhorova, N. A.; Spivak, A. Yu., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 10, p. 1858 - 1863
  作者：Tolstikov, G. A.、Prokhorova, N. A.、Spivak, A. Yu.、Khalilov, L. M.、Sultanmuratova, V. R.

  DOI：——

  日期：——
• Glycosylidene Carbenes, Part 29 , Insertion into B−C and Al−C Bonds: Glycosylborinates, -boranes, and -alanes
  作者：Wolfgang Wenger、Andrea Vasella

  DOI：10.1002/1522-2675(20000705)83:7<1542::aid-hlca1542>3.0.co;2-f

  日期：2000.7.5

  Insertion of the glycosylidene carbenes derived from the diazirines 1, 14 and 15 into the B-alkyl bond of the B-alkyl-9-oxa-10-borabicyclo[3.3.2]decanes 5, 6, and 7 yielded the stable glycosylborinates 8/9 (55%, 55:45), 10/11 (31%, 65:35), 12/13 (47%, 60:40), 16/17 (55%, 55:45), 18/19 (47%, 45:55), and 20/21 (31%, 30:70). Crystal-structure analysis of 17 and NOEs of 9 and 19 show that 17 9, and 19 adopt similar conformations. The glycosylborinates are stable under acidic, basic and thermal conditions. The unprotected glycosylborinate 25 was obtained in 80% by hydrogenolysis of 12. Insertion of the glycosylidene carbene derived from the diazirine 1 into a B-C bond of BEt3, BBu3, and BPh3 led to unstable glycosylboranes that were oxidised to yield the hemiacetals 29 (55%), 31 (45%), and 33 (48%), respectively, besides the glucals 30 (13%), 32 (20%), and 34 (20%), respectively. Insertion of the glycosylidene carbenes derived from 14 and 15 into a B - C bond of BEt3 led exclusively to hemiacetals; only 15 yielding traces of the glucal 40 besides the hemiacetal 39. The glycosylidene carbene derived from 1 reacted with AL(Bu-1), and AlMe3 to generate reactive glycosylalanes that were hydrolysed, yielding the C-glycosides 46 (21%) and 49 (30%), respectively besides the glucals 48 (26%) and 51 (30%); deuteriolysis instead of protonolysis led to the monodeuterio analogues of 46 and 49, respectively, which possess an equatorial H-2-atom at the anomeric center.
• TOLSTIKOV, G. A.;PROXOROVA, N. A.;SPIVAK, A. YU., 5 BCEC. KONF. PO METALLOORGAN. XIMII, YURMALA, 1-4 APR., 1991: TEZ. DOKL.+
  作者：TOLSTIKOV, G. A.、PROXOROVA, N. A.、SPIVAK, A. YU.

  DOI：——

  日期：——