[(2R,3S,4R)-4-乙酰氧基-3-[(2R,3R,4S,5R,6R)-3,4,5-三乙酰氧基-6-(乙酰氧基甲基)四氢吡喃-2-基]氧基-3,4-二氢-2H-吡喃-2-基]甲基乙酸酯 | 67314-34-5

• 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
• 中文名称: [(2R,3S,4R)-4-乙酰氧基-3-[(2R,3R,4S,5R,6R)-3,4,5-三乙酰氧基-6-(乙酰氧基甲基)四氢吡喃-2-基]氧基-3,4-二氢-2H-吡喃-2-基]甲基乙酸酯
• 英文名称: hexa-O-acetyl-D-maltal
• 英文别名: per-O-acetyl-D-maltal；2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl-(1,4)-3,6-di-O-acetyl-α-D-glycal；(2R,3R,4S,5R,6R)-2-(((2R,3S,4R)-4-acetoxy-2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate；Hexa-O-acetylmaltal；[(2R,3S,4R)-4-acetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 67314-34-5
• 化学式: C₂₄H₃₂O₁₅
• 分子量: 560.509
• InChiKey: RCDAESHZJBZWAW-LYDSDTOKSA-N

物化性质

• 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)：
  -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：
  0.67
• 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
• 危险类别码：
  R24/25
• 储存条件：
  存于阴凉干燥处。

SDS

Name:	Hexa-O-acetyl-maltal Material Safety Data Sheet
Synonym:
CAS:	67314-34-5

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

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
67314-34-5	Hexa-O-acetyl-maltal		unlisted

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

---

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.

---

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.

---

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.

---

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.

---

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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 67314-34-5: 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.

---

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

---

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, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 67314-34-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Hexa-O-acetyl-maltal - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

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# 67314-34-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 67314-34-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 67314-34-5 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  β-D-麦芽糖八乙酸酯	2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate	22352-19-8	C28H38O19	678.598
  alpha-D-麦芽糖八乙酸酯	D-maltose octaacetate	6920-00-9	C28H38O19	678.598
  麦芽糖	Maltose	16984-36-4	C12H22O11	342.3
  D-(+)-纤维二糖	Maltose	133-99-3	C12H22O11	342.3

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  (2R,3R,4S,5S,6R)-2-[[(2R,3S,4R)-4-羟基-2-(羟基甲基)-3,4-二氢-2H-吡喃-3-基]氧基]-6-(羟基甲基)四氢吡喃-3,4,5-三醇	maltal	32447-71-5	C12H20O9	308.285

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R)-4-乙酰氧基-3-[(2R,3R,4S,5R,6R)-3,4,5-三乙酰氧基-6-(乙酰氧基甲基)四氢吡喃-2-基]氧基-3,4-二氢-2H-吡喃-2-基]甲基乙酸酯 在 吡啶 、 Selectfluor 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl-(1,4)-1,3,6-tri-O-acetyl-2-deoxy-2-fluoro-D-gluco-mannopyranose
  参考文献：
  名称：

  Synthesis of 2-deoxy-2,2-difluoro-α-maltosyl fluoride and its X-ray structure in complex with Streptomyces coelicolor GlgEI-V279S

  摘要：

  结核分枝杆菌（Mtb）的GlgE是一个经过基因验证的结核病药物靶点，参与α-葡聚糖生物合成。本文描述的Streptomyces coelicolor（Sco）的GlgEI-V279S变异体被用作基于结构的抑制剂设计的模型酶。

  DOI：

  10.1039/c5ob00867k
• 作为产物：
  描述：

  麦芽糖 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 [(2R,3S,4R)-4-乙酰氧基-3-[(2R,3R,4S,5R,6R)-3,4,5-三乙酰氧基-6-(乙酰氧基甲基)四氢吡喃-2-基]氧基-3,4-二氢-2H-吡喃-2-基]甲基乙酸酯
  参考文献：
  名称：

  一种2-硝基糖烯的合成方法

  摘要：

  本发明公开一种2‑硝基糖烯的合成方法，属于糖的合成技术领域。所述2‑硝基糖烯结构如下：。其次，本发明还提供上述2‑硝基糖烯的制备方法，本发明提供的制备方法经过一步合成即可高效的制备2‑硝基糖烯。

  公开号：

  CN113200951B

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。
• Me₃SI-promoted chemoselective deacetylation: a general and mild protocol
  作者：Aakanksha Gurawa、Manoj Kumar、Sudhir Kashyap

  DOI：10.1039/d1ra03209g

  日期：——

  Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developed via employing KMnO4 as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses

  通过使用 KMnO4 作为添加剂，开发了一种 Me3SI 介导的简单而有效的乙酰基化学选择性脱保护方案。这种化学选择性脱乙酰化适用于多种底物，可耐受碳水化合物、氨基酸、天然产物、杂环化合物和一般支架中的多种敏感官能团。该协议很有吸引力，因为它使用环境友好的试剂系统在环境条件下进行定量和清洁转化。
• C-Glycosyl Tyrosines. Synthesis and Incorporation into <i>C</i>-Glycopeptides
  作者：Alan J. Pearce、Sharn Ramaya、Simon N. Thorn、Graham B. Bloomberg、Daryl S. Walter、Timothy Gallagher

  DOI：10.1021/jo990253e

  日期：1999.7.1

  The synthesis of the Fmoc-protected C-glycosyl tyrosines 1 and 2, together with two other related C-glycosyl tyrosines, has been achieved. Key reactions involved (i) the reaction of a glycal with an organozinc reagent (carrying an aryl iodide function) in the presence of a Lewis acid to establish the C-glycosyl linkage and (ii) subsequent cross coupling of the aryl iodide to an alanyl zinc reagent

  已经实现了Fmoc保护的C-糖基酪氨酸1和2以及另外两种相关的C-糖基酪氨酸的合成。关键反应涉及（i）在路易斯酸存在下，糖基与有机锌试剂（具有芳基碘化物的功能）反应，以建立C-糖基键合；以及（ii）随后将芳基碘化物交叉偶联到丙氨酰基上锌试剂（在Pd（0）催化剂存在下）完成α-氨基酸部分的构建。使用固相肽合成方法，将两个甘露糖基衍生物1（显示为L-Tyr [C-Ac（4）-alpha-D-Man]）（含四个甘氨酸）掺入线性六肽中3，然后将其转换为C（2）对称环状寡肽4。
• 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。
• Palladium(<scp>ii</scp>)-catalyzed stereoselective synthesis of <i>C</i>-glycosides from glycals with diaryliodonium salts
  作者：Kumar Bhaskar Pal、Jiande Lee、Mrinmoy Das、Xue-Wei Liu

  DOI：10.1039/d0ob00247j

  日期：——

  An efficient palladium(II) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including D-glucal, D-galactal, D-allal, L-rhamnal, L-fucal, L-arabinal, D-maltal, and D-lactal, occurred effectively and the corresponding

  描述了有效的钯（II）介导的二芳基碘鎓盐对糖的C-糖基化，为合成具有优异立体选择性的2,3-二脱氧C-芳基糖苷提供了新的策略。所述Ç不同范围的烯糖的-glycosylation，包括d -glucal，d -galactal，d -allal，大号-rhamnal，大号-fucal，大号-arabinal，d -maltal，和d -lactal，有效地发生，并且相应的C-β-糖苷以中等至良好的产率获得。由于丰富的官能团相容性，广泛的底物范围和出色的α-立体选择性，该方案被认为是对碳水化合物化学领域的重要补充。