D-半乳醛环3,4-碳酸 | 149847-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 中文名称: D-半乳醛环3,4-碳酸
• 英文名称: 3,4-o-carbonyl-D-galactal
• 英文别名: D-Galactal cyclic 3,4-carbonate；(3aR,4R,7aR)-4-(hydroxymethyl)-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-one
• CAS: 149847-26-7
• 化学式: C₇H₈O₅
• 分子量: 172.138
• InChiKey: WFLPBXPPOHMBIT-HSUXUTPPSA-N

物化性质

• 熔点：
  −34 °C(lit.)
• 沸点：
  440.4±45.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : D-Galactal cyclic 3,4-carbonate
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 149847-26-7
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C7H8O5
Molecular Weight : 172,14 g/mol
CAS-No. : 149847-26-7
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. Use respirators and components tested and approved under
appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing -34 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: -1,042
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  D-半乳醛环3,4-碳酸 在 4-二甲氨基吡啶 、 二甲基二环氧乙烷 、 sodium hydride 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.0h， 生成 Acetic acid (3aS,4R,6S,7R,7aS)-4-benzyloxymethyl-6-((2R,3R,4R)-2-benzyloxymethyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-3-yloxy)-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
  参考文献：
  名称：

  寡糖合成策略：在 KH-1（腺癌）抗原的简明全合成中的应用

  摘要：

  已经实现了标题化合物的简洁且可能实用的合成。该路线具有高度的收敛性和合成操作的经济性。一个关键步骤是在所需的羟基受体位点同时引入三个 α-l-岩藻糖残基（参见 37 → 39）。实现了与载体蛋白的缀合，并完成了包括用于研究抗体特异性的截短结构的途径。

  DOI：

  10.1021/ja9725864
• 作为产物：
  描述：

  1,5-anhydro-6-O-(tert-butyldimethylsilyl)-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到D-半乳醛环3,4-碳酸
  参考文献：
  名称：

  钯催化糖基化立体选择性合成β- N-糖基磺酰胺的一般策略

  摘要：

  公开了通过钯催化的脱羧烯丙基化，在3，4- O-碳酸碳酸酯与N-甲苯磺酰基官能化的脂族和芳族胺之间的高效且温和的糖基化反应。各种高官能度的2，3-不饱和β- N-糖苷以良好的产率提供，并具有良好的区域选择性和立体选择性。另外，还研究了糖基磺酰胺作为组装功能性衍生物的前体的应用，包括糖基化，二羟基化和向N-糖苷的亲核加成。

  DOI：

  10.1021/acs.orglett.8b01506

文献信息

• Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides
  作者：Shuai Meng、Wenhe Zhong、Wang Yao、Zhongjun Li

  DOI：10.1021/acs.orglett.0c00732

  日期：2020.4.17

  A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent

  描述了在温和条件下由二苯基二硒化物和苯基碘（III）双（三氟乙酸酯）介导的糖衍生物的苯基硒糖基化反应。立体选择性糖基化反应是通过在这些糖基上安装熔融碳酸盐来实现的。3,4- ø -碳酸酯galactals和2,3- ö -碳酸酯2- hydroxyglucals被转换成对应于良好的产率具有优良的β选择性糖苷，产生2- phenylseleno -2-脱氧-β半乳糖苷和2- phenylseleno -β-甘露糖苷分别是2-脱氧-β-半乳糖苷和β-甘露糖苷的良好前体。
• Facile and stereospecific synthesis of diverse β-<i>N</i>-glycosyl sulfonamide scaffolds <i>via</i> palladium catalysis
  作者：Lei Zhong、Qunliang Wang、Yujuan Wang、Yiyang Cheng、Yimeng Xiong、Haibo Peng、Zhen Zhou、Yun He、Yuanwei Dai

  DOI：10.1039/d3cc04063a

  日期：——

  Glycosylation is an important strategy to improve the druggability of lead compounds. Here, we present a palladium-catalysed stereospecific N-glycosylation of sulfonamides. This approach stands out with wide substrate scope, high functional group tolerance, and easy scalability, furnishing a broad spectrum of densely functionalized β-N-glycosyl sulfonamides with good efficiency and exceptional reg

  糖基化是提高先导化合物成药性的重要策略。在这里，我们提出了磺酰胺的钯催化立体特异性N-糖基化。该方法具有底物范围广、官能团耐受性高和易于扩展的优点，提供了广泛的密集功能化 β- N-糖基磺酰胺，具有良好的效率和卓越的区域/立体选择性。通过后期多样化策略和产品的各种简单合成转化，构建了多种类药物糖磺酰胺支架。总的来说，所建立的方案为有效制备糖基磺酰胺以促进药物发现提供了有价值的工具。
• 10.1021/acs.orglett.4c02466
  作者：Xiong, Yimeng、Dai, Yuanwei

  DOI：10.1021/acs.orglett.4c02466

  日期：——

  An efficient and practical glycosylation platform for synthesizing N-glycosides by leveraging palladium catalysis is disclosed. This approach enables facile access to diverse heterocyclic N-glycosides with excellent regio- and stereoselectivities and high site selectivity of multiple N atoms. The reaction exhibits a broad substrate scope (65 examples), high functional group tolerance, and easy scalability

  公开了一种利用钯催化合成N-糖苷的高效实用的糖基化平台。这种方法能够轻松获得多种杂环N-糖苷，具有优异的区域和立体选择性以及多个N原子的高位点选择性。该反应具有广泛的底物范围（65 个实例）、高官能团耐受性和易于扩展性。其合成效用通过药学相关分子的后期功能化和糖苷产品的各种非对映选择性转化得到证明。总的来说，我们的方法为有效和立体控制合成有价值的N-糖基化杂环提供了一个方便的工具。
• Stereoselective O-Glycosylation of Glycals with Arylboronic Acids Using Air as the Oxygen Source
  作者：Qiuyuan Wang、Mengnan Lai、Huajun Luo、Keke Ren、Jingrui Wang、Nianyu Huang、Zhangshuang Deng、Kun Zou、Hui Yao

  DOI：10.1021/acs.orglett.1c04378

  日期：2022.3.4
• Multivalent Templated Saccharides:  Convenient Syntheses of Spacer-Linked 1,1‘-Bis -and 1,1‘,1‘‘-Tris-β-glycosides by the Glycal Epoxide Glycosidation Method
  作者：Raymond J. Patch、Hang Chen、Chennagiri R. Pandit

  DOI：10.1021/jo961819r

  日期：1997.3.1