1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 | 2595-05-3

• 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: 1,2:5,6-二异亚丙基-alpha-D-异呋喃糖
• 中文别名: 1,2:5,6-双-O-异丙叉基-α-D-异呋喃糖；1,2:5,6-二-O-异亚丙基-α-D-呋喃阿洛糖；1,2,5,6-二异亚丙基-a-D-异呋喃糖；1,2:5,6-二异亚丙基-α-D-异呋喃糖；双丙酮-D-阿洛糖；双丙酮阿洛糖；1,2,5,6-二异亚丙基-alpha-D-异呋喃糖
• 英文名称: Diacetone D-glucose
• 英文别名: 1,2-5,6-di-O-isopropylidene-α-D-allofuranose；1,2:5,6-di-O-isopropylidene-D-allofuranose；1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose；(3aR,5S,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: 2595-05-3
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: KEJGAYKWRDILTF-VVULQXIFSA-N

物化性质

• 熔点：
  73-76 °C(lit.)
• 比旋光度：
  37.5 º (c=1,chloroform)
• 沸点：
  363.54°C (rough estimate)
• 密度：
  1.2377 (rough estimate)
• 溶解度：
  在甲苯中几乎透明
• 稳定性/保质期：

  如果按照规定使用和储存，则不会发生分解。

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

• 危险品标志：
  Xi
• 安全说明：
  S22
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2932999099
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封于2-8℃阴凉干燥处保存。

SDS

Name:	1 2:5 6-Di-O-Isopropylidene-Alpha-D-Allofuranose 98% Material Safety Data Sheet
Synonym:	None known
CAS:	2595-05-3

Section 1 - Chemical Product MSDS Name:1 2:5 6-Di-O-Isopropylidene-Alpha-D-Allofuranose 98% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2595-05-3	1,2,5,6-Di-O-Isopropylidene-1-D-Allof	98	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2595-05-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 74.00 - 76.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H20O6
Molecular Weight: 260.28

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2595-05-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,2,5,6-Di-O-Isopropylidene-1-D-Allofuranose - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 2595-05-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2595-05-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2595-05-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

现在含吡喃环的色满衍生物1,2:5,6-二异亚丙基-α-D-异呋喃糖已经在TFT液晶材料中得到了广泛的应用。此外，它还可以用作医药中间体、碳水化合物、生化试剂、修饰糖环、呋喃和糖类化合物等其他生化试剂。

制备

将硼氢化钠（1.6 g，42.3 mmol）在冷却至0℃的条件下分批加入到1,2:5,6-二-O-异亚丙基-α-D-呋喃葡萄糖-3-果糖1（4.22 g，16.34 mmol）的乙醇-水溶液（10:1，116 mL）中。继续搅拌直至薄层层析（TLC）显示反应完全（大约需要3小时）。然后通过加入饱和氯化铵水溶液中和反应混合物，并在减压下小心除去乙醇。向剩余物中加入水，并用二氯甲烷萃取所得混合物四次。合并的有机提取物经硫酸钠干燥并浓缩，最终得到粗结晶1,2:5,6-二异亚丙基-α-D-异呋喃糖。

反应信息

• 作为反应物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 D-allose
  参考文献：
  名称：

  分子内氢键（PO -H）稳定六元环磷酸酯的座椅构型

  摘要：

  设计，合成并通过NMR和计算方法研究了带有内部被保护或未被保护的羟基的六元环状磷酸酯（2-苯氧基-2-氧代-1,3,2-二氧杂膦酰基）。在BF 3 ·OEt 2的存在下，用三乙基硅烷或三甲基烯丙基硅烷可在主要位点选择性打开O-异亚丙基保护的1,2-二醇。施加到5,6- Õ -isopropylidenepentofuranosides，该反应产生了在形成对应-1,3-二醇前体的用于包含六元环磷酸盐ø -异丙基或ö -1,1-二甲基-3-丁烯基C-6的官能团。该Ø用BF 3 ·OEt 2进行磷酸化后，有效地除去了-1,1-二甲基-3-丁烯基保护基，得到了具有游离羟基的六元环状磷酸酯。具有顺着磷酸基顺式取向的游离羟基的环状磷酸酯显示出邻位偶合常数3 J HP，其与椅子构型一致。这是由于形成了稳定椅子构象的七元分子内氢键合的环状结构。因此，内部氢键相互作用减弱了苯氧基在轴向位置上的强烈趋势。计算研究为实验观察提供了有力的支持。

  DOI：

  10.1021/jo050753+
• 作为产物：
  描述：

  D-glucose 在 sodium hypochlorite 、 sodium tetrahydroborate 、 2,2,6,6-四甲基哌啶氧化物 、 磷酸 、 碳酸氢钠 、 potassium bromide 、 zinc(II) chloride 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 1,2:5,6-二异亚丙基-alpha-D-异呋喃糖
  参考文献：
  名称：

  [EN] NOVEL PROCESS FOR MAKING ALLOFURANOSE FROM GLUCOFURANOSE
  [FR] NOUVEAU PROCÉDÉ DE FABRICATION D'ALLOFURANOSE À PARTIR DE GLUCOFURANOSE

  摘要：

  本发明涉及从描述和权利要求中定义的葡糖呋喃糖中制备阿洛呋喃糖。阿洛呋喃糖是合成寡核苷酸时的中间体，可用作药物。

  公开号：

  WO2019224172A1

文献信息

• [EN] AMINOGLYCOSIDES AND USES THEREOF<br/>[FR] AMINOGLYCOSIDES ET LEURS UTILISATIONS
  申请人：ACHAOGEN INC

  公开号：WO2019046126A1

  公开（公告）日：2019-03-07

  Provided herein are aminoglycoside compounds, such as compounds of formula (I), (II), (III), (IV), (IVa), (V), (VI), (VIIa), or (VIIb) or pharmaceutically acceptable salts, solvates, stereoisomers, or tautomers of any of the foregoing, useful as therapeutic or prophylactic agents. Also provided herein are methods for their preparation. The compounds may be useful in treating a bacterial infection in a subject, for example a Gram-negative bacterial infection.

  本文提供了氨基糖苷化合物，例如式(I)、(II)、(III)、(IV)、(IVa)、(V)、(VI)、(VIIa)或(VIIb)的化合物，或者上述任何一个的药用盐、溶剂化合物、立体异构体或互变异构体，可用作治疗或预防剂。本文还提供了它们的制备方法。这些化合物可能在治疗受试者的细菌感染方面有用，例如革兰氏阴性细菌感染。
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2018006063A1

  公开（公告）日：2018-01-04

  Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

  用于治疗细菌感染的组合物和方法包括含有环七肽二聚体与一个或多个单糖或寡糖基团结合的化合物。特别是，这些化合物可用于治疗由革兰氏阴性细菌引起的细菌感染。
• β-Oxygen Effect in the Barton–McCombie Deoxygenation Reaction: Further Experimental and Theoretical Findings
  作者：Alma Sánchez-Eleuterio、Jacinto Sandoval-Lira、Jenny García-Sánchez、Lorena Monterrosas-Pérez、Julio M. Hernández-Pérez、Leticia Quintero、Fernando Sartillo-Piscil

  DOI：10.1021/jo4012943

  日期：2013.9.20

  of the bond undergoing cleavage and this with the two C–O antibonding orbitals anti oriented. Such molecular orbital interactions are not present in the α-ribo-furanose; therefore, the β-scission is highly delayed, and due to the reversibly nature of the stannyl radical addition, the ribo-furanose xanthate is forced to take an alternative route: the homolytic substitution (SH2) of the sulfide sulfur

  研究了在锡烷基自由基存在下衍生自木糖和核糖呋喃糖衍生物的（S）-甲基黄药的化学性质。衍生自β-木糖呋喃糖的黄药仅提供脱氧产物；而在相同的反应条件下，α-核糖呋喃糖黄药衍生物可定量生成半硫缩醛化合物。我们认为，在β-木糖的情况下-呋喃糖衍生物，在Barton-McCombie脱氧反应中具有良好的β-氧作用，根据理论计算，在该反应中存在异常的分子轨道相互作用（而不是先前提出的应变）。这些轨道相互作用涉及SOMO（由苯乙烯基自由基加成产生的中间产物）与正经历裂解的键的σ*轨道，以及与两个取向相反的C-O反键轨道。这种分子轨道相互作用不存在于α-核糖呋喃糖中。因此，β分裂的延迟被大大延迟，并且由于甲锡烷基自由基添加的可逆性，核糖呋喃酮黄原酸酯被迫采取另一种途径：均质取代（S H2）对硫化物硫有锡烷基自由基。这种自由基加成产生了烷氧基硫代羰基，该自由基在消除羰基硫之前被Bu 3 SnH所捕获。随后，
• Diastereoselective deprotonative metalation of chiral ferrocene derived acetals and esters using mixed lithium–cadmium and lithium–zinc combinations
  作者：Gandrath Dayaker、Aare Sreeshailam、D. Venkata Ramana、Floris Chevallier、Thierry Roisnel、Shinsuke Komagawa、Ryo Takita、Masanobu Uchiyama、Palakodety Radha Krishna、Florence Mongin

  DOI：10.1016/j.tet.2014.02.010

  日期：2014.3

  derivative in 74% yield with 90% de (SP diastereoisomer) using the base generated from CdCl2 and Li(TMP) (3 equiv), and in 85% yield with 91% de (SP diastereoisomer) through a double asymmetric induction using a chiral lithium–zinc base generated from ZnCl2·TMEDA and lithium (R)-bis(1-phenylethyl)amide (4 equiv). In contrast, using a combination prepared from ZnCl2 and Li(TMP) (4 equiv) with the ferrocene carboxylate

  原位双金属组合，尤其是由MCl 2（TMEDA）（M = Zn，Cd; TMEDA = N，N，N'，N'-四甲基乙二胺）和Li（TMP）（3或4当量，TMP = 2筛选了（2,6,6-四甲基哌啶子基）具有手性基团的非对映选择性去质子化二茂铁的能力。使用由CdCl 2和Li（TMP）（3当量）生成的碱，由双丙酮d-葡萄糖生成的二茂铁羧酸盐以74％的产率提供90％的de（S P非对映异构体）相应的2-碘衍生物。收率91％de（S P非对映异构体）通过使用由ZnCl 2 ·TMEDA和锂（R）-双（1-苯乙基）酰胺（4当量）生成的手性锂锌基双不对称诱导。相比之下，使用由ZnCl 2和Li（TMP）（4当量）制备的组合物与由6-（叔丁氧羰基氨基）-6-脱氧-3- O-甲基-1,2- O-异亚丙基获得的二茂铁羧酸盐-α- d -glucofuranose导致ř P分离之后碘在57％衍生物的产率。在分离的S
• Molecular Recognition at the Active Site of Catechol‐ <i>O</i> ‐methyltransferase (COMT): Adenine Replacements in Bisubstrate Inhibitors
  作者：Manuel Ellermann、Ralph Paulini、Roland Jakob‐Roetne、Christian Lerner、Edilio Borroni、Doris Roth、Andreas Ehler、W. Bernd Schweizer、Daniel Schlatter、Markus G. Rudolph、François Diederich

  DOI：10.1002/chem.201003648

  日期：2011.5.27

  inhibitors in ternary complexes with COMT and Mg2+ confirm our predicted binding mode of the adenine replacements. The cocrystal structure of an inhibitor bearing no nucleobase can be regarded as an intermediate along the reaction coordinate of bisubstrate inhibitor binding to COMT. Our studies show that solvation varies with the type of adenine replacement, whereas among the adenine derivatives, the nitrogen

  L- Dopa是帕金森氏病的标准治疗药物，可被儿茶酚-O-甲基转移酶（COMT）灭活。COMT催化活化的甲基从S腺苷甲硫氨酸（SAM）转移到其邻苯二酚底物，例如L-多巴，存在镁离子。对COMT SAM结合位点的分子识别特性仅进行了稀疏的研究。在这里，我们通过双底物抑制剂的腺嘌呤部分的结构改变来探索该位点。由于该核碱基在生物系统中的丰富性和重要性，对腺嘌呤的分子识别特别受关注。新型的腺嘌呤替代双底物抑制剂是通过基于结构的设计开发的，并使用了由Vorbrüggen及其同事引入的核苷化方案进行合成。用放射化学测定法测量腺嘌呤部分与COMT的关键相互作用。几种双底物抑制剂，最著名的是腺嘌呤替代品硫代吡啶，嘌呤，N对于低至6 n M的COMT ，甲基腺嘌呤和6甲基嘌呤显示出纳摩尔的IC 50值（中位抑制浓度）。与COMT和Mg 2+形成三元复合物的双底物抑制剂的一系列六个共晶体结构证实了我们预测的腺