7,8-dideoxy-1,2:3,4-di-O-isopropylidene-6(S)-hydroxy-α-D-galacto-oct-7-inopyranose | 4977-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 7,8-dideoxy-1,2:3,4-di-O-isopropylidene-6(S)-hydroxy-α-D-galacto-oct-7-inopyranose
• 英文别名: 7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose；O¹,O²;O³,O⁴-diisopropylidene-β-L-glycero-D-galacto-7,8-dideoxy-oct-7-ynopyranose；(1S)-1-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]prop-2-yn-1-ol
• CAS: 4977-08-6
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: LRJOBRZMNVOYJI-KTWSDMTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7,8-dideoxy-1,2:3,4-di-O-isopropylidene-6(S)-hydroxy-α-D-galacto-oct-7-inopyranose 生成 [(1R)-1-[(1S,2R,6R,8S,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]prop-2-ynyl] 4-nitrobenzoate
  参考文献：
  名称：

  JAROSZ, S.;GLODEK, J.;ZAMOJSKI, A., CARBOHYDR. RES., 163,(1987) N 2, 289-296

  摘要：

  DOI：
• 作为产物：
  描述：

  7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-7-ynopyranos-6-ulose 生成 7,8-dideoxy-1,2:3,4-di-O-isopropylidene-6(S)-hydroxy-α-D-galacto-oct-7-inopyranose
  参考文献：
  名称：

  JAROSZ, SLAWOMIR, BULL. POL. ACAD. SCI. CHEM., 35,(1987) N 5-6, 161-169

  摘要：

  DOI：

文献信息

• Synthesis of higher-carbon sugars via vinyltin derivatives of simple monosaccharides
  作者：Sławomir Jarosz

  DOI：10.1016/0008-6215(87)80058-7

  日期：1987.9

  Abstract 6- O -Benzyl-7,8-dideoxy-1,2:3,4-di- O -isopropylidene- l - glycero -α- d - galacto -oct-7-ynopyranose reacted with tributyltin hydride to afford ( Z -6- O -benzyl-7,8-dideoxy-1,2:3,4-di- O -isopropylidene-8-(tributylstannyl)- l - glycero -α- d - galacto -oct-7-enopyranose, which was subsequently isomerized to the E -olefin 4 . Replacement of the tributyltin moietey with lithium in 4 afforded

  通过将它们分别转化成3-O-苄基-1,2-O-异亚丙基-α-d-葡萄糖-和-β-1-l-呋喃糖来确定新的手性中心在6和7中的构型。6和7的氧化得到相同的烯酮3-O-苄基-6-C-[（（E））-6-O-苄基-7-脱氧-1,2：3,4-二-O-异亚丙基-1 -甘油-α-d-半乳聚糖-七吡喃酮-7-亚萘基] -6-脱氧-1，2-O-异亚丙基-α-d-木糖-己呋喃诺斯-5-ulose。
• Stereochemistry of diels-alder reaction at high pressure: asymmetric induction in the reaction of 1-methoxybuta-1,3-diene with sugar aldehydes
  作者：Janusz Jurczak、Tommasz Bauer、Sławomir Jarosz

  DOI：10.1016/s0040-4020(01)88110-2

  日期：1986.1

  High-pressure (4+2)cycloaddition of 1-methoxybuta-1,3-diene () to three representative sugar aldehydes , , and in the presence and without Eu(fod)3 was studied. The effects of pressure and catalyst on asymmetric induction were examined. Stereochemical models were used for interpretation of the results.

  1-methoxybuta -1,3-二烯（的高压（4 + 2）环加成），以三种代表性糖醛，以及在存在和不铕（FOD）3进行了研究。检查了压力和催化剂对不对称感应的影响。立体化学模型用于解释结果。
• Synthesis of C-substituted triazoles, isoxazoles, and pyrazoles by 1,3-dipolar cycloaddition to acetylenic sugars
  作者：Derek Horton、Tsai Ji-Hsiung

  DOI：10.1016/s0008-6215(00)84125-7

  日期：1978.12

  Abstract Addition of phenyl azide to 3,5-di-O-acetyl-6,7-dideoxy-1,2-O-isopropylidene-β- l -idio-hept-6-ynofuranose (1) and subsequent saponification gave a 4-substituted 1-phenyl-1,2,3-triazole derivative (3) whose optical rotatory dispersion (o.r.d.) curve was positive. The α- d -gluco analog (5) of 1 similarly gave the 5-epimer (7) of 3; its o.r.d. curve was negative. Both 3 and 7 were degraded

  摘要将叠氮化物添加到3,5-二-O-乙酰基-6,7-二脱氧-1,2-O-异亚丙基-β-1-二-庚基-6-呋喃糖（1）中，随后进行皂化，得到4旋光色散（ord）曲线为正的被取代的1-苯基-1,2,3-三唑衍生物（3）。类似的1的α-d-葡萄糖类似物（5）给出3的5表位（7）; 它的ord曲线为负。3和7均降解为已知的1-苯基-1,2,3-三唑-4-甲醛。类似地，将2,4,6-三甲基苄腈N-氧化物加至1或5中，得到相应的结晶3-甲磺酰异恶唑，为单一产物。使用13C-nmr光谱确定添加的方向。从1,2：3,4-二-O-异亚丙基-d-甘油-α-d-半乳糖-辛-7-吡喃葡萄糖（10）及其l-甘油6中获得了相关的3-甲苯并恶唑（11和13）。 -epimer（12）分别；11表示预期的大水平旋转，而6顶点的13也是左旋转的。由1-（α-氯亚苄基）-2-苯基肼和碱原位制备的苯甲腈（N-苯基）亚胺不会与1
• Stereospecific synthesis of 5,6-dihydro-2H-pyran system. High-pressure cycloaddition of 1:2,3:4-di-0-isopropylidene- α-D-galactopyranose-6-ulose to 1-methoxybuta-1,3-diene
  作者：Janusz Jurczak、Tomasz Bauer、Sławomir Jarosz

  DOI：10.1016/s0040-4039(01)81526-4

  日期：——

  The high-pressure cycloaddition of 1:2,3:4-di-0-isopropylidene- α-D-galactopyranos-6-ulose (3) to 1-methoxybuta-1,3-diene (1) afforded diastereoisomerically pure cycloadduct 4 whose absolute configuration was determined.

  将1：2,3：4-二-0-异亚丙基-α-D-吡喃半乳糖-6-果糖（3）高压环加成1-甲氧基丁1,3-二烯（1）得到非对映异构纯的环加合物4确定了其绝对配置。
• Organotransition metal modified sugars 14. Activation of sugar-based alkynols at a metal carbonyl template: a metal vinyl carbene functionalization of carbohydrates and non-conventional route to organometallic disaccharides
  作者：Karl Heinz Dötz、Daphne Paetsch、Hubert Le Bozec

  DOI：10.1016/s0022-328x(99)00295-8

  日期：1999.10

  Chromium and tungsten alkenyl carbene modified carbohydrates have been synthesized by activation of sugar-based propargylic alcohols with pentacarbonyl-THF complexes followed by addition of methanol. This method has also been exploited in disaccharide synthesis. Higher functionalized carbohydrate skeletons are accessible by Diels-Alder and Michael-type addition reactions. (C) 1999 Elsevier Science S.A. All rights reserved.