7,8-dideoxy-1,2:3,4-di-O-isopropylidene-6(R)-hydroxy-α-D-galacto-oct-7-inopyranose | 4640-85-1

• 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(R)-hydroxy-α-D-galacto-oct-7-inopyranose
• 英文别名: O¹,O²;O³,O⁴-diisopropylidene-α-D-glycero-D-galacto-7,8-dideoxy-oct-7-ynopyranose；(1R)-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: 4640-85-1
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: LRJOBRZMNVOYJI-PQTSNVLCSA-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(R)-hydroxy-α-D-galacto-oct-7-inopyranose 生成 [(1S)-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(R)-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

• New Synthetic Bromination Procedures for Use in Radiolabelling-Chemistry: Reaction ofC-Metallated Derivatives of Carbohydrates with Bromide, in the Presence of Mild Oxidizing Agents
  作者：Jean-Richard Neeser、Laurance D. Hall、Julius A. Balatoni

  DOI：10.1002/hlca.19830660403

  日期：1983.6.15

  triglycosylborane 1 and dicyclohexylglycosylborane 2 readily react with bromine chloride generated in situ from bromide and N-chlorosuccinimide (NCS) to give the bromo-sugar 3 (75 and 60%, resp.). The use of the BH3-THF/bromide/NCS/2 AcONa procedure permits the rapid, face-specific synthesis of 6 (58% uptake of bromine) and face-selective synthesis of 8/9 (71% uptake of bromine), from vinyl ether derivatives

  在2摩尔当量的存在下。对于AcONa，三糖基硼烷1和二环己基糖基硼烷2均易于与由溴化物和N-氯代琥珀酰亚胺（NCS）原位产生的氯化溴反应，得到溴糖3（分别为75％和60％）。BH 3 -THF /溴化物/ NCS / 2 AcONa程序的使用可实现快速的面特异性合成6（溴的吸收率为58％）和面选择性合成8/9（溴的吸收率为71％），分别来自乙烯基醚衍生物5和7。二环己基硼烷/溴化物/ NCS / 2 AcONa方法可快速定量地转化11至溴糖12（91％）。硼氢化-反金属化序列使获得C-化的碳水化合物13（71％）和14（78％）成为可能。通过与一当量的溴化物/氯胺-T / HCl水溶液反应，自然裂解双（糖基）汞衍生物13，得到3（87％）和14（76％）。炔糖15的氢化锡烷基化得到（E）-锡烷基乙烯基衍生物16作为主要产物。后者的前体16被溴化物/氯胺-T / HCl水溶液试剂自发裂解，得到溴丁糖。17（96％）。
• 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
• Synthesis, crystal structure, and conformation of 1(S)-acetoxy-3-[6(R)-O-benzyl-1,2:3,4-di-O-isopropylidene-α-d-galactopyranos-6-yl]-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-d-galactopyranosid-6-yl)propyne
  作者：Janusz W. Krajewski、Przemysław Gluziński、Sławomir Jarosz、Aleksander Zamojski、Jānis Bleidelis、Anatolii Mishnyov、Andrejas Ķemme

  DOI：10.1016/s0008-6215(00)90668-2

  日期：1985.12

  295(1), c = 20.547(3) A, and β = 102.66(1)°. The structure was solved by direct methods and refined by a full-matrix, least-squares procedure against 3839 unique reflections (F > 2σ F ), resulting in a final R = 0.045 (unit weights). The configuration at the new chiral center (C-1) was established as S ( d ). The galactopyranose rings have conformations 4 C 1 (tri- O -benzylated moiety) and ° S 5 + °

  摘要6-O-苄基-7,8-二脱氧-1,2：3,4-二-O-异亚丙基-d-甘油-α-d-半乳糖基-oct-7-吡喃葡萄糖与2,3,3-甲基苯甲基的缩合4-三-O-苄基-6-脱氧-β-d-半乳糖-庚二醛-1,5-吡喃糖苷提供3- [6（ R）-O-苄基-1,2：3,4-二-O-异亚丙基-α-d-吡喃半乳糖-6-基] -1-羟基-1-（甲基2,3,4-三-O-苄基-6-脱氧-β-d-吡喃半乳糖苷-6-基）丙炔。通过X射线衍射法在四圆衍射仪中研究了1a的1-O-乙酰基衍生物（1c）的单晶。化合物1c在单斜晶系系统中结晶，空间群P2 1（Z = 2），晶胞尺寸为a = 14.896（2），b = 8.295（1），c = 20.547（3）A和β= 102.66（1）° 。通过直接方法对结构进行了解析，并通过全矩阵对其进行了细化，最小二乘程序针对3839个唯一反射（F>2σF），最终的R = 0.0
• 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.
• (6<i>S</i>)-8-<i>C</i>-Chloro-6,7,8-trideoxy-1,2:3,4-di-<i>O</i>-isopropylidene-α-<scp>D</scp>-<i>galacto</i>-octa-6,7-dienopyranose
  作者：D. Horton、Q. Liu、R. L. Luck、J. V. Silverton

  DOI：10.1107/s0108270196012851

  日期：1997.2.15

  The title structure, C14H19ClO5, consists of an allene substituted with a Cl atom at one end joined at the other end to a D-galactopyranose ring bearing two fused isopropylidene groups.