4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-lyxo-hept-2-enononitrile | 120085-63-4

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-lyxo-hept-2-enononitrile
• 英文别名: [(2R,3R,4R)-3,4-diacetyloxy-6-cyano-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 120085-63-4
• 化学式: C₁₃H₁₅NO₇
• 分子量: 297.265
• InChiKey: OPOUWJFXZRRHOV-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 安全说明：
  S24/25

SDS

Name:	4 5 7-Tri-O-acetyl-2 6-anhydro-3-deoxy-D-l yxo-hept-2-enononitrile Material Safety Data Sheet
Synonym:
CAS:	120085-63-4

Section 1 - Chemical Product MSDS Name:4 5 7-Tri-O-acetyl-2 6-anhydro-3-deoxy-D-l yxo-hept-2-enononitrile Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
120085-63-4	4,5,7-Tri-O-acetyl-2,6-anhydro-3-deoxy		unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 120085-63-4: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid or liquid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C13H15NO7
Molecular Weight: 297.26

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 120085-63-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4,5,7-Tri-O-acetyl-2,6-anhydro-3-deoxy-D-l yxo-hept-2-enononitrile - 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.
WGK (Water Danger/Protection)
CAS# 120085-63-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 120085-63-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 120085-63-4 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

反应信息

• 作为反应物：
  描述：

  4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-lyxo-hept-2-enononitrile 在 dichlorotetrakis(dimethylsulfoxide)ruthenium 、 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantane choride 作用下， 以 水 为溶剂， 反应 2.0h， 以72%的产率得到4,5,7-三邻乙酰基-2,6-酐-3-脱氧-d-lyxo-2-氨基庚烯
  参考文献：
  名称：

  在水介质中使用钌配合物将糖基氰化物化学选择性水合为C-糖基甲酰胺

  摘要：

  将[RuCl 2（DMSO）4 ]中的存在Ñ -benzylated 1,3,5-三氮杂-7-磷有效地催化糖基氰化物的水合为相应的甲酰胺衍生物在水或水ñ在105甲基吡咯烷酮溶剂混合物℃。已表明O-乙酰基，O-苯甲酰基和O-苄基保护基，端基溴和叠氮化物取代基以及双键与这些反应条件相容。

  DOI：

  10.1016/j.tetlet.2015.09.040
• 作为产物：
  描述：

  (2R,3S,4R,5S,6S)-2-(乙酰氧基甲基)-6-氰基四氢-2H-吡喃-3,4,5-三基三乙酸酯 在 molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以69%的产率得到4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-lyxo-hept-2-enononitrile
  参考文献：
  名称：

  3-deoxy-d- lyxo -2-heptulosaric acid（DHA）衍生物的首次合成

  摘要：

  到的3-脱氧-D-甲基糖苷的甲基酯的合成路线来苏-heptulosaric酸（13）由1- cyanogalactal开始2进行说明。后一种物质是通过在二氯甲烷中使用1,8-二氮杂双环[5.4.0]十一烷基-7-烯直接从1中除去乙酸来制备的。

  DOI：

  10.1016/0040-4020(95)00150-7

文献信息

• Unprecedented β-manno type thiodisaccharides with a C-glycosylic function by photoinitiated hydrothiolation of 1-C-substituted glycals
  作者：László Lázár、László Juhász、Gyula Batta、Anikó Borbás、László Somsák

  DOI：10.1039/c6nj03751h

  日期：——

  and cyano) substituted glycals with a range of sugar derived thiols gave the corresponding β-manno type 3-deoxy-3-S-disaccharides with full regio- and stereoselectivity. The configuration of the glycals (arabino vs. lyxo) and the size of the protecting groups had no significant effect on the outcome of the transformations. Formation of by-products was tracked down by LCMS studies and correlated with

  自由基hydrothiolation ö -peracylated 1-C-（氨基甲酰基，甲氧基羰基和氰基）取代的烯糖与一系列的糖衍生的硫醇，得到相应的β-甘露键入3-脱氧-3-小号具有完全区域选择性-disaccharides和立体选择性。糖基的构型（阿拉伯糖vs. lyxo）和保护基的大小对转化的结果没有显着影响。通过LCMS研究追踪了副产物的形成，并将其与双键的电子密度相关联，以表明反应对于COOMe，特别是CONH 2基团作为1-C取代基是合成有用的。
• Remarkable Oxidation Stability of Glycals: Excellent Substrates for Cerium(IV)-Mediated Radical Reactions
  作者：Torsten Linker、Dirk Schanzenbach、Elangovan Elamparuthi、Thomas Sommermann、Werner Fudickar、Viktor Gyóllai、László Somsák、Wolfgang Demuth、Michael Schmittel

  DOI：10.1021/ja8052706

  日期：2008.11.26

  rationale, which might be important for the redox behavior of other allylic systems. Finally, donors and acceptors in the 1-position exert the strongest influence on the oxidation stability, shifting the potentials by almost 1 V and resulting in different follow-up reactions of the cerium(IV)-mediated additions of malonates. It is the remarkable oxidation stability of glycals that makes them valuable

  通过它们在溶液中的氧化还原数据、计算的 HOMO 能量以及添加在硝酸铈 (IV) 铵存在下产生的亲电子自由基的行为，糖醛在氧化条件下的显着稳定性变得明显。获得了高达 2.03 V 与二茂铁的氧化电位，这对于环状烯醇醚来说非常高，但与自由基反应的反应时间密切相关。保护基团对氧化稳定性和糖类的 HOMO 能有很大影响，因为 E(ox) 从 O-甲硅烷基经过 O-苄基转移到 O-乙酰基超过 500 mV。有趣的是，这种效应必须通过 sigma 键传递，甚至高达苯甲酸酯基团的对位，正如碳水化合物中远程取代基的广泛变化所证实的那样。提出了相邻 CO 键的 sigma*-轨道与双键的 HOMO 的有利相互作用作为机械原理，这对于其他烯丙基系统的氧化还原行为可能很重要。最后，1 位的供体和受体对氧化稳定性的影响最大，将电位移动了近 1 V，并导致铈 (IV) 介导的丙二酸酯添加的不同后续反应。糖醛显着的
• The first general synthesis of 2-<i>C</i>-(β-<scp>d</scp>-glycopyranosyl)pyrimidines and their evaluation as inhibitors of some glycoenzymes
  作者：Eszter Szennyes、Éva Bokor、Peter Langer、Gyöngyi Gyémánt、Tibor Docsa、Ádám Sipos、László Somsák

  DOI：10.1039/c8nj04035d

  日期：——

  A systematic study was performed on the preparation of unknown 2-C-(β-D-glucopyranosyl)pyrimidines. Pinner type cyclisation of O-perbenzylated C-(β-D-glucopyranosyl)formamidine with β-ketoesters, dimethyl malonate, and β-diketone derived α,β-unsaturated β-chloroketones followed by catalytic hydrogenation resulted in various substituted 2-C-(β-D-glucopyranosyl)-pyrimidin-4(3H)-ones, and 2-C-(β-D-glucopyranosyl)-4

  对未知的2- C-（β- D-吡喃葡萄糖基）嘧啶的制备进行了系统的研究。的平纳型环化ö -perbenzylated Ç - （β- d吡喃葡萄糖基）甲脒与β酮酯，丙二酸二甲酯，和β二酮衍生的α，β不饱和β氯酮，接着通过催化氢化导致的各种取代的2- Ç - （β- D-吡喃葡萄糖基）-嘧啶-4（3 H）-一和2- C-（β- D-吡喃葡萄糖基）-4,6-二取代-嘧啶，分别以中等至良好的产率。上述嘧啶衍生物也通过未保护的环闭环而获得。C-（β- D-吡喃葡萄糖基）甲idine具有相同的1,3-二亲电子试剂。此外，还精心设计了一个连续的一锅三步程序，该程序从O-过酰基化的D-氨基葡萄糖基氰化物开始，以可接受的糖总收率（25-94％）得到具有各种糖构型的上述嘧啶的代表。由于所应用的1,3-二亲电子试剂的多功能性，这些合成路线代表了获得目标化合物的第一种可扩展方法。新C-glycopyranosy
• Preparation of C-(2-deoxyhex/pent-1-enopyranosyl)heterocycles
  作者：Saad H. Mahmoud、László Somsák、István Farkas

  DOI：10.1016/0008-6215(94)84245-0

  日期：1994.2

  )benzothiazoles also gave 2-(per-O-acetyl-2-deoxyhex/pent-1-enopyranosyl)benzothiazole s with DBU. 3-(Per-O-acetylhexo/pentopyranosyl)-[1,2,4]triazolo[4,3-a] pyrimidines rearranged with DBU to the corresponding acetylated 2-glycosyl-[1,2,4]triazolo[1,5-a]pyrimidines. By the reaction of 1-cyano-D-galactal with ammonium azide, 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)tetr azole was prepared

  通过用1,8-二氮杂双环[5.4.0]直接从适当的乙酰化2,6-脱水庚烷/己腈中除去乙酸，制得乙酰化的1-氰基葡萄糖（2,6-脱水-3-脱氧庚烷/己-2-烯腈）非质子溶剂中的]十一烷基-7-烯（DBU）。乙酰化的1-氰基-D-半乳糖的氰基与2-氨基硫酚的杂环化导致2-（3,4,6-三-O-乙酰基-2-脱氧-D-lyxo-hex-1-enopyranosyl）苯噻唑。几种2-（全-O-乙酰基己基/戊吡喃糖基）苯并噻唑还与DBU一起产生了2-（全-Oo乙酰基-2-脱氧己基/戊-1-烯吡喃基）苯并噻唑。DBU将3-（Per-O-乙酰基己基/戊吡喃糖基）-[1,2,4]三唑并[4,3-a]嘧啶重排为相应的乙酰化2-糖基-[1,2,4]三唑并[1， 5-a]嘧啶。通过1-氰基-D-半乳糖与叠氮化铵的反应，2-（3,4，
• Acetylated 1-cyano and 1-cyano-2-hydroxy derivatives of d-galactal and d-arabinal
  作者：László Somsák

  DOI：10.1016/0008-6215(89)85101-8

  日期：1989.12

  Synthese des composes du titre a partir de cyanure de bromo-1 tetra-O-acetyl-2,3,4,6 galactopyranosyle (ou de son analogue D-arabino) traite avec de la poudre de zinc dans l'acide acetique (ou avec du cyanure de mercure dans le nitromethane)

  合成了溴化氰1部分四-O-乙酰基2,3,4,6吡喃半乳糖（或类似物D-阿拉伯糖）的特征氰甲烷的氰化物