hexa-O-acetyl-D-lactal | 51450-24-9

• 物质功能分类: 生物化工 - 糖类化合物 - 寡糖
• 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: hexa-O-acetyl-D-lactal
• 英文别名: hexa-O-acetyl lactal；3,6,2',3',4',6'-hexa-O-acetyl-D-lactal；per-O-acetyl-D-lactal；2',3,3',4',6,6'-hexa-O-acetyl-D-lactal；3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucal；Hexa-O-acetyl-lactal；[(2R,3S,4R)-4-acetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 51450-24-9
• 化学式: C₂₄H₃₂O₁₅
• mdl: MFCD00037582
• 分子量: 560.509
• InChiKey: RCDAESHZJBZWAW-AXHDHDPASA-N

物化性质

• 熔点：
  109-111°C
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  15

安全信息

• 安全说明：
  S24/25
• 储存条件：
  Freezer (-20°C)

SDS

Name:	Hexa-O-acetyl-lactal Material Safety Data Sheet
Synonym:
CAS:	51450-24-9

Section 1 - Chemical Product MSDS Name:Hexa-O-acetyl-lactal Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
51450-24-9	Hexa-O-acetyl-lactal		unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Moisture sensitive.Light sensitive.
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 tightly closed container. Store in a dry area. Freeze.
Store under argon.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 51450-24-9: 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: C24H32O15
Molecular Weight: 560.51

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 51450-24-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Hexa-O-acetyl-lactal - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 51450-24-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 51450-24-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 51450-24-9 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：

  hexa-O-acetyl-D-lactal 在 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 、 碘 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 46.0h， 生成 4-pentenyl 2-acetamido-3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A convenient access to β-glycosides of N-acetyllactosamine

  摘要：

  Iodoacetoxylation of 3,6-di-0-acetyI-4-0-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (hexa-O-acetyllactal) and the corresponding hexa-O-benzoyl derivative, gave the alpha-1,2-trans 1-O-acetyl-2-deoxy-2-iodo adducts with high stereoselectivity and good yields. These were treated with an excess of trimethylsilyl azide in the presence of trimethylsilyl trifluoromethanesulfonate affording the corresponding alpha-1,2-trans 2-deoxy-2-iodoglycosyl azides. In the presence of an alcohol, a Staudinger reaction at the anomeric azide ledin situ to an iminophosphorane which rearranged with elimination of iodine at C-2. The aziridine intermediate thus obtained reacted with a suitable alcohol to afford the corresponding lactosamine beta-glycosides. The reaction occurred with double inversion of configuration at C-1 and C-2. Deprotection of the amine functionality and further transformation into the acetamido derivatives could be achieved without isolation of the intermediates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00263-7
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 碘 、 二氯二茂钛 、 锰 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 1.17h， 以87%的产率得到hexa-O-acetyl-D-lactal
  参考文献：
  名称：

  聚甲基氢硅氧烷 (PMHS)：碘/硅烷组合试剂合成应用的便捷选择 - 直接进入 2-羟基糖化以及葡萄糖醛酸和氨基葡萄糖的有用构建块

  摘要：

  在大量合成过程中，聚甲基氢硅氧烷 (PMHS) 被证明是三乙基硅烷的实用替代品，这些合成过程需要使用碘/硅烷组合试剂快速生成糖基碘。此外，该组合试剂的范围扩大到特别快速生成 2-乙酰氧基糖醛，以及快速合成 D-葡萄糖醛酸和 D-葡萄糖胺的有用结构单元。所有合成目标都在特别短的时间内通过一锅法或通过实验序列获得，无需费力的中间体色谱纯化。

  DOI：

  10.1002/ejoc.201201084

文献信息

• Studies on the Reaction of D-Glucal and its Derivatives with 1-Chloromethyl-4-Fluoro-1,4-Diazoniabicyclo[2.2.2]Octane Salts
  作者：J. Ortner、M. Albert、H. Weber、K. Dax

  DOI：10.1080/07328309908543997

  日期：1999.1.1

  ABSTRACT The reaction of D-glucal and its derivatives with the electrophilic N-F-fluorination reagents F-TEDA tetrafluoroborate and triflate was studied by means of 19F NMR spectroscopy. In all cases mixtures of 2-deoxy-2-fluoro-D-gluco- and -D-mannopyranose derivatives were formed, the ratio of which was dependent on the nature of the O-protecting groups. Concerning the products arising from the direct

  摘要利用19F NMR光谱研究了D-葡萄糖及其衍生物与亲电NF-氟化试剂F-TEDA四氟硼酸酯和三氟甲磺酸酯的反应。在所有情况下，均形成2-脱氧-2-氟-D-葡萄糖-和-D-甘露吡喃糖衍生物的混合物，其比例取决于O-保护基团的性质。关于直接通过双键添加试剂产生的产物，D-葡萄糖构型的化合物（13-20）通常显示出比其D-甘露聚糖对应物（21-28）更高的水解速率。仅当形成单个端基异构体（例如2,4-二硝基苯基糖苷29e / 37e和二糖氟化物35d / 43d）或过氧乙酸酯（例如29f / 37f）时，才能实现产品分离。
• Synthesis of Benzaldehyde-Functionalized Glycans: A Novel Approach Towards Glyco-SAMs as a Tool for Surface Plasmon Resonance Studies
  作者：Sebastian Kopitzki、Knud J. Jensen、Joachim Thiem

  DOI：10.1002/chem.200902693

  日期：——

  In recent years the interest in tools for investigating carbohydrate–protein (CPI) and carbohydrate‐carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self‐assembled monolayers (SAM) of

  近年来，人们对研究碳水化合物-蛋白质（CPI）和碳水化合物-碳水化合物相互作用（CCI）的工具的兴趣大大增加。为了调查CPI和CCI，可以使用几种采用不同链接方法的技术。表面等离振子共振（SPR）成像是分析碳水化合物衍生物可模仿糖萼的自组装单分子膜（SAM）形成的最合适工具。与先前用于分析CPI和CCI的SPR成像方法相反，本文报道的新颖方法可轻松，快速地合成接头间隔子和碳水化合物衍生物，并通过控制配体的数量和方向来增强结合作用。为了通过还原胺化固定在具有生物排斥性的氨基官能化SPR芯片上，已通过包括烯烃复分解在内的几个简便步骤合成了多种醛官能化的聚糖结构（葡萄糖，半乳糖，甘露糖，葡糖胺，纤维二糖，乳糖和乳糖胺）。提出了针对凝集素伴刀豆球蛋白A的有效固定方法和首次结合研究。
• Copper mediated iodoacetoxylation and glycosylation: effective and convenient approaches for the stereoselective synthesis of 2-deoxy-2-iodo glycosides
  作者：Suresh Kumar Battina、Sudhir Kashyap

  DOI：10.1016/j.tetlet.2016.01.035

  日期：2016.2

  Copper(II) triflate catalyzed stereoselective glycosylation of 2-iodo-glycosyl acetate donor is reported. Anomeric activation of 2-deoxy-1-O-acetyl sugar employing Cu(OTf)2 found to be an attractive as well effective alternative reagent to the most frequently used triflic acid (TfOH) source such as TMSOTf or TBSOTf. Scope of the reaction was explored for various aglycones. This protocol involves simple

  报道了三氟甲磺酸铜（II）催化2-碘-糖基乙酸乙酸酯供体的立体选择性糖基化。发现使用Cu（OTf）2的2-脱氧-1- O-乙酰基糖的端基活化是最常用的三氟甲磺酸（TfOH）来源（如TMSOTf或TBSOTf）的诱人且有效的替代试剂。探索了各种糖苷配基的反应范围。该方案涉及简单的反应操作，采用较便宜且无毒的试剂系统，并且能够立体选择性地制备2-脱氧-2-碘-糖苷。此外，CuI / NaIO 4在环境温度下在AcOH的存在下促进了各种糖类的区域选择性碘乙酰氧基化，从而获得了2-碘-糖基乙酸酯。
• Novel stereocontrolled amidoglycosylation of alcohols with acetylated glycals and sulfamate ester
  作者：Teiichi Murakami、Yukari Sato、Kyoko Yoshioka、Mutsuo Tanaka

  DOI：10.1039/c4ra02367f

  日期：——

  A regio- and stereo-controlled, one-pot amidoglycosylation of alcohols has been achieved using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene in the presence of a rhodium(ii) catalyst.

  一种区域和立体控制的一锅法醇的酰胺基糖苷化反应已经通过在铑（II）催化剂存在下使用O-乙酰基基卡尔、三氯乙氧基磺酰胺和碘苯酚实现。
• Convenient stereocontrolled amidoglycosylation of alcohols with acetylated glycals and trichloroethoxysulfonamide
  作者：Teiichi Murakami、Yukari Sato、Kyoko Yoshioka、Mutsuo Tanaka

  DOI：10.1016/j.carres.2016.09.001

  日期：2016.11

  of alcohols has been developed using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene. This one-pot amidoglycosylation was applied to a variety of primary and secondary alcohols to afford the beta-O-glycosides with acceptable yields up to 84%. The reaction would proceed via stereoselective intermolecular aziridination of the glycal from the alpha-face followed by SN2 reaction with

  使用O-乙酰基化的糖，三氯乙氧基磺酰胺和碘代苯，已经开发出了区域和立体控制的铑（II）催化的醇酰胺糖基化反应。将这种一锅式酰胺基糖基化反应应用于各种伯醇和仲醇，以高达84％的可接受收率得到β-O-糖苷。该反应将通过α面的糖的立体选择性分子间叠氮化进行，然后与β面的C-1处的醇进行SN2反应，仅得到1,2：2,3-二-反式取代的异构体。