二丙酮-D-葡萄糖 | 14686-89-6

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 二丙酮-D-葡萄糖
• 英文名称: (1,2:5,6)-di-O-isopropylidene-D-gulose
• 英文别名: 1,2:5,6-di-O-isopropylidene-α-D-gulofuranose；1,2:5,6-Di-O-isopropyliden-α-D-gulofuranose；O¹,O²,O⁵,O⁶-Diisopropyliden-α-D-gulofuranose；1,2:5,6-Di-O-isopropylidene-alpha-D-gulofuranose；(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 14686-89-6
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: KEJGAYKWRDILTF-HOTMZDKISA-N

物化性质

• 熔点：
  110-111 °C(lit.)
• 沸点：
  362.8±42.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  2
• 海关编码：
  29400090,29329970
• 危险类别码：
  R36/37/38
• RTECS号：
  LZ4958000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  二丙酮-D-葡萄糖 在 吡啶 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 72.5h， 生成 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside
  参考文献：
  名称：

  Novel 4′-Branched Nucleosides

  摘要：

  Total chemical synthesis of 4'-hydroxymethylnucleosides with an additional modification in a sugar residue was developed. The synthesis was made by condensation of corresponding protected sugars and nucleic bases with subsequent deprotection. In such a way 3'-azido- and 3'-amino-3'deoxy-4'-hydroxymethylribonucleosides, 2',3'-anhydroribo- and 2',3'-anhydrolyxo-4'-hydroxymethylribonucleosides as well as 3'-deoxy-4'hydroxymethylribollucleosides were prepared. At concentrations up to 100 mu M none of them inhibited reproduction of human immunodeficiency virus type 1 in H9 and PBL cells as well as human herpes simplex virus type 2 and human cytomegalovirus in vero cells.

  DOI：

  10.1080/15257779408013221
• 作为产物：
  描述：

  双丙酮葡萄糖 在 ruthenium trichloride 、 sodium tetrahydroborate 、 potassium metaperiodate 、 Celite 、 ammonium chloride 、 potassium carbonate 作用下， 生成 二丙酮-D-葡萄糖
  参考文献：
  名称：

  （–）-litsenolides C-1和C-2的总合成

  摘要：

  描述了由D-葡萄糖以12％的总收率合成（-）-litsenolides C 1和C 2的方法，其中α-亚烷基双键是通过C-2含碳水合物衍生物的Wittig反应形成的。

  DOI：

  10.1039/p19870002681

文献信息

• The rapid synthesis of deoxyfluoro sugars using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)
  作者：Bogdan Doboszewski、George W. Hay、Walter A. Szarek

  DOI：10.1139/v87-070

  日期：1987.2.1

  Deoxyfluoro sugars were synthesized rapidly by the reaction of trifluoromethanesulfonyl derivatives of partially protected sugars with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) under mild conditions. The displacements occurred with inversion of configuration; fluorine has been introduced stereospecifically at each of the secondary alcoholic sites of aldohexopyranosides and in one

  脱氧氟糖是通过部分保护糖的三氟甲磺酰基衍生物与三（二甲氨基）锍二氟三甲基硅酸盐（TASF）在温和条件下反应快速合成的。位移发生于构型反转；在吡喃醛糖苷的每个二级醇位点和呋喃类系统的一个例子中，氟已被立体定向​​地引入。在某些情况下，会产生不含氟的不饱和化合物。
• α-Hydrogen elimination in some carbohydrate triflates
  作者：Ahmed El Nemr、Tsutomu Tsuchiya

  DOI：10.1016/0040-4039(95)01607-j

  日期：1995.10

  In some carbohydrate triflates, treatment with MeLi (or BuLi) in ether caused α-hydrogen elimination initially, then the resulting carbanion is stabilized to give either C-methyl(or butyl)-hydroxy derivatives or unsaturated products.

  在一些碳水化合物三氟甲磺酸酯中，用乙醚中的MeLi（或BuLi）处理首先引起α-氢消除，然后将所得的碳负离子稳定化，得到C-甲基（或丁基）-羟基衍生物或不饱和产物。
• Studies on synthesis of 3-O-alkyl-D-glucose and 3-O-alkyl-D-allose derivatives and their biological activities.
  作者：TETSURO IKEKAWA、KAZUHIKO IRINODA、KOICHI SAZE、TATSUHIKO KATORI、HIDEAKI MATSUDA、MASANORI OHKAWA、MARTIN KOSIK

  DOI：10.1248/cpb.35.2894

  日期：——

  Twenty two 3-Ο-alkyl derivatives of D-glucose and D-allose, four 3-Ο-alkenyl derivatives of D-glucose having an end methylene group, and four 3-Ο-ω-hydroxyalkyl- or -methoxyalkyl derivatives of D-glucose were synthesized. Their cytotoxicity in vitro against the cultured leukemia L-5178Y cell line, antimicrobial activity and plant growth-inhibitory effect were determined.

  合成了二十二种D-葡萄糖和D-阿洛糖的3-O-烷基衍生物、四种末端甲撑基的D-葡萄糖3-O-烯基衍生物和四种D-葡萄糖的3-O-ω-羟基烷基或-甲氧基烷基衍生物。测定了它们对体外培养的白血病L-5178Y细胞的细胞毒性、抗菌活性和植物生长抑制作用。
• Inactivation of <i>S</i>-Adenosyl-<scp>l</scp>-homocysteine Hydrolase and Antiviral Activity with 5‘,5‘,6‘,6‘-Tetradehydro-6‘-deoxy-6‘-halohomoadenosine Analogues (4‘-Haloacetylene Analogues Derived from Adenosine)
  作者：Morris J. Robins、Stanislaw F. Wnuk、Xiaoda Yang、Chong-Sheng Yuan、Ronald T. Borchardt、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm980163m

  日期：1998.9.1

  intermediates were deprotected to give the 6'-chloro 3a, 6'-bromo 3b, and 6'-iodo 3c acetylenic nucleoside analogues. Iodo compound 3c appears to inactivate S-adenosyl-L-homocysteine hydrolase by a type I ("cofactor depletion") mechanism since complete reduction of enzyme-bound NAD+ to NADH was observed and no release of adenine or iodide ion was detected. In contrast, incubation of the enzyme with the chloro 3a

  用硝酸银和N-碘代琥珀酰亚胺（NIS）处理受保护的9-（5，6-二脱氧-β-D-核糖基-己基-5-ynofuranosyl）腺嘌呤衍生物并脱保护，得到6'-碘炔基核苷类似物3c。3-O-苯甲酰基-5,6-二脱氧-1，2-O-异亚丙基-α-D-核糖-六-5-烯呋喃糖的卤代反应生成6-卤代炔糖，将其转化为异头的1,2-二-邻乙酰基衍生物，并与6-N-苯甲酰腺嘌呤偶联。将这些中间体脱保护，得到6'-氯3a，6'-溴3b和6'-碘3c炔属核苷类似物。碘化合物3c似乎通过I型（“辅因子耗竭”）机制使S-腺苷-L-高半胱氨酸水解酶失活，因为观察到酶结合的NAD +完全还原为NADH，并且未检测到腺嘌呤或碘离子的释放。相比之下，将酶与氯3a或溴3b类似物一起温育会导致Cl-或Br-和Ade的释放，以及E-NAD +部分还原为E-NADH。化合物3a，3b和3c抑制牛痘病毒，水泡性口炎病毒，副流感3病毒和
• δ-Lactams: synthesis from<scp>D</scp>-glucose, and preliminiary evaluation as a fucosidase inhibitor, of<scp>L</scp>-fuconic-δ-lactam
  作者：George W. J. Fleet、Nigel G. Ramsden、Raymond A. Dwek、Tom W. Rademacher、Linda E. Fellows、Robert J. Nash、Donovan St. C. Green、Bryan Winchester

  DOI：10.1039/c39880000483

  日期：——

  Polyhydroxylated δ-lactams are a potential class of glycosidase inhibitors; the synthesis of L-fuconic-δ-lactam (7), which preliminary studies have shown to be a weak but specific α-L-fucosidase inhibitor, is described.

  多羟基化δ-内酰胺是一类潜在的糖苷酶抑制剂；本文描述了L-夫糖酸δ-内酰胺（7）的合成，初步研究表明其是一种弱但特异性的α-L-岩藻糖苷酶抑制剂。