5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone | 94324-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone
• 英文别名: (3aR,6S,6aS)-6-(bromomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one；(3aR,6S,6aS)-6-(bromomethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 94324-23-9
• 化学式: C₈H₁₁BrO₄
• 分子量: 251.077
• InChiKey: ZSWDFLIWNDCXNU-HSUXUTPPSA-N

物化性质

• 熔点：
  85-89 °C
• 密度：
  1.6453 (rough estimate)
• 溶解度：
  可溶于丙酮、二氯甲烷、乙酸乙酯、甲醇
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25

SDS

Name:	5-Bromo-5-Deoxy-2 3-O-Isopropylidene-D-Ribonolactone 99% Material Safety Data Sheet
Synonym:	None Known
CAS:	94324-23-9

Section 1 - Chemical Product MSDS Name:5-Bromo-5-Deoxy-2 3-O-Isopropylidene-D-Ribonolactone 99% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
94324-23-9	5-Bromo-5-Deoxy-2,3-O-Isopropylidene-D	99%	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 breathing is difficult, give oxygen. Get medical aid. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. 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. Keep refrigerated. (Store below 4C/39F.)

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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# 94324-23-9: 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:
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
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 87.00 - 89.00 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: C8H11BrO4
Molecular Weight: 251.08

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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, hydrogen bromide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 94324-23-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Bromo-5-Deoxy-2,3-O-Isopropylidene-D-Ribonolactone - 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# 94324-23-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 94324-23-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 94324-23-9 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：

  5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 作用下， 以 苯 为溶剂， 生成 ethyl 2-[(3aS,4S,6R,6aR)-6-(acetyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]acetate
  参考文献：
  名称：

  New syntheses of carbocycles from carbohydrates. Cyclization of radicals derived from unsaturated halo sugars

  摘要：

  DOI：

  10.1021/jo00204a029
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 四溴化碳 、 三苯基膦 作用下， 生成 5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone
  参考文献：
  名称：

  抑制阿拉伯糖5-磷酸异构酶。一种抑制细菌脂多糖生物合成的方法。

  摘要：

  5-磷酸阿拉伯糖（A5P）异构酶是脂多糖生物合成中的关键酶，脂多糖是革兰氏阴性细菌外膜的重要组成部分。设想异构酶的机理涉及烯二醇中间体。测试了一系列与底物或中间体类似的化合物作为A5P异构酶的抑制剂，并认为良好的抑制剂会阻止细菌生长或使细胞更易受其他抗生素或自然防御作用。在一系列磷酸化糖中，异构酶抑制活性的顺序如下：醛糖酸大于醛糖醇大于醛糖。非磷酸化糖的抑制作用要小得多。最好的抑制剂是4-磷酸赤藓酸（54），Km / Ki = 29。

  DOI：

  10.1021/jm00372a003

文献信息

• Inhibition of arabinose 5-phosphate isomerase. An approach to the inhibition of bacterial lipopolysaccharide biosynthesis
  作者：Eric C. Bigham、Charles E. Gragg、William R. Hall、John E. Kelsey、William R. Mallory、Drew C. Richardson、Charles Benedict、Paul H. Ray

  DOI：10.1021/jm00372a003

  日期：1984.6

  Arabinose 5-phosphate ( A5P ) isomerase is a key enzyme in the biosynthesis of lipopolysaccharide, an essential component of the outer membrane of Gram-negative bacteria. The mechanism of the isomerase is envisioned to involve an enediol intermediate. A series of compounds, which are analogues of the substrates or intermediate, were tested as inhibitors of A5P isomerase with the belief that a good

  5-磷酸阿拉伯糖（A5P）异构酶是脂多糖生物合成中的关键酶，脂多糖是革兰氏阴性细菌外膜的重要组成部分。设想异构酶的机理涉及烯二醇中间体。测试了一系列与底物或中间体类似的化合物作为A5P异构酶的抑制剂，并认为良好的抑制剂会阻止细菌生长或使细胞更易受其他抗生素或自然防御作用。在一系列磷酸化糖中，异构酶抑制活性的顺序如下：醛糖酸大于醛糖醇大于醛糖。非磷酸化糖的抑制作用要小得多。最好的抑制剂是4-磷酸赤藓酸（54），Km / Ki = 29。
• Studies on the chemoselectivity and diastereoselectivity of samarium(II) iodide mediated transformations of carbohydrate derived ω-halo-α,β-unsaturated esters
  作者：Sharon M. Bennett、Raphinos Kouya Biboutou、Zhihong Zhou、Robert Pion

  DOI：10.1016/s0040-4020(98)00191-4

  日期：1998.5

  Some carbohydrate derived ω-bromo- and ω-iodo- α,β- unsaturated esters were reduced with SmI2 under a variety of conditions. The chemoselectivity varies dramatically with the choice of solvent system, the identity of halogen atom, the type of ester used, the geometry of the double bond, and the oxygenation pattern of the substrate. The stereoselectivity of the SmI2 mediated reactions is also influenced

  在各种条件下，SmI 2还原了一些碳水化合物衍生的ω-溴-和ω-碘-α，β-不饱和酯。化学选择性随溶剂系统的选择，卤素原子的身份，所用酯的类型，双键的几何形状以及底物的氧化方式而有很大不同。SmI 2介导的反应的立体选择性也受反应参数的影响。
• Synthesis of (1R,2S,3R,4R)-2,3,4-trihydroxycyclopentylamine from D-ribonolactone
  作者：Anthony H. Ingall、Peter R. Moore、Stanley M. Roberts

  DOI：10.1039/c39940000083

  日期：——

  A seven-step procedure for the transformation of ribonolactone 3 into the aminotriol 12 can be effected in 28% overall yield.

  将核糖内酯3转化为氨基三醇12的七步程序可以获得28%的总收率。
• 3-Amino-2-piperidones as constrained pseudopeptides: Preparation of a new Ser-Leu surrogate
  作者：Jordi Piró、Mario Rubiralta、Ernest Giralt、Anna Diez

  DOI：10.1016/s0040-4039(99)00897-7

  日期：1999.6

  We describe a stereoselective preparation of 3-amino-2-piperidone 1, a new conformationally constrained Ser-Leu surrogate. The key steps of the synthesis of compound 1 are the lactamisation of the secondary aminolactone 4 and the amination of the 3-position via the sulfite 2. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Haefele, Brigitte; Schroeter, Detlef; Jaeger, Volker, Angewandte Chemie, 1986, vol. 98, # 1, p. 89 - 90
  作者：Haefele, Brigitte、Schroeter, Detlef、Jaeger, Volker

  DOI：——

  日期：——

表征谱图