3,4-二-O-乙酰基-6-O-(叔丁基二甲基甲硅烷基)-D-半乳醛 | 136656-49-0

• 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: 3,4-二-O-乙酰基-6-O-(叔丁基二甲基甲硅烷基)-D-半乳醛
• 中文别名: 3,4-DI-O-乙酰基-6-O-(叔丁基二甲基甲硅烷基)-D-半乳醛
• 英文名称: 3,4-di-O-acetyl-1,5-anhydro-6-O-t-butyldimethylsilyl-2-deoxy-D-lyxo-hex-1-enitol
• 英文别名: 3,4-Di-O-acetyl-1,5-anhydro-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-lyxo-hex-1-enitol；3,4-di-O-acetyl-6-O-(tert-butyldimethylsilyl)-D-galactal；3,4-Di-acetyl-6-o-(tert-butyldimethylsilyl)-d-galactal；[(2R,3R,4R)-3-acetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl] acetate
• CAS: 136656-49-0
• 化学式: C₁₆H₂₈O₆Si
• 分子量: 344.48
• InChiKey: HSYXDFIWVSUKFT-RBSFLKMASA-N

物化性质

• 沸点：
  278 °C(lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 3,4-Di-O-acetyl-6-O-(tert-butyldimethylsilyl)-D-
galactal
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. : 136656-49-0
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.
Label elements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C16H28O6Si
Molecular Weight : 344,48 g/mol
CAS-No. : 136656-49-0
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, silicon 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.
Recommended storage temperature: -20 °C
Specific end use(s)
Apart 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 no data available
point
f) Initial boiling point and 278 °C
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- no data available
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
Do not store near acids., 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

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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：

  3,4-二-O-乙酰基-6-O-(叔丁基二甲基甲硅烷基)-D-半乳醛 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol
  参考文献：
  名称：

  Mereyala, Hari Babu; Venkataramanaiah, Kanamarlapudi C, Journal of Chemical Research, Miniprint, 1991, # 8, p. 1953 - 1966

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3R,4R)-2-(羟基甲基)-3,4-二氢-2H-吡喃-3,4-二醇 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3,4-二-O-乙酰基-6-O-(叔丁基二甲基甲硅烷基)-D-半乳醛
  参考文献：
  名称：

  Oxidation of Fully Protected Glycals by Hypervalent Iodine Reagents

  摘要：

  A new application of organoiodine(III) is presented. Fully protected glycals are directly converted into 2,3-dihydro-4H-pyran-4-ones by [hydroxy(tosyloxy)iodo]benzene (PhI(OH)OTs, 1). The detailed study reveals that this conversion is independent of the relative stereochemistry as well as the nature of protection on the pyran ring. 3-O-Silyl groups are most smoothly converted into the keto group giving 2,3-dihydro-4H-pyran-4-ones in yields up to 74%. In contrast, 4,6-di-O-acetyl-3-deoxyglucal (19) affords the rearranged oxidation product 32. Both observations can be reconciled by the proposed mechanism.

  DOI：

  10.1021/jo00110a028

文献信息

• Practical synthesis of 2-deoxy sugars <i>via</i> metal free deiodination reactions
  作者：Wang Yao、Hao Wang、Jing Zeng、Qian Wan

  DOI：10.1080/07328303.2021.2015365

  日期：2021.11.22

  Abstract 2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction by using cyclohexane and ethyl acetate as co-solvent is reported. This is an environmentally benign protocol, which operates smoothly under

  摘要 2-脱氧糖苷，其中 C-2 羟基被氢原子取代，是许多生物活性天然产物和药物分子中的重要基序。本文报道了一种使用环己烷和乙酸乙酯作为共溶剂的改进的过氧化二月桂酰介导的自由基脱碘反应。这是一种对环境无害的方案，可在温和条件下平稳运行，并允许以高达 98% 的收率有效制备一系列 2-脱氧糖苷。
• Product Analysis in the Iodine(III)-Promoted Oxidation of Carbohydrate-Derived Cyclic Enol Ethers: A Mechanistic Study
  作者：Jan Harders、Alfons Garming、Alexander Jung、Volker Kaiser、Holger Monenschein、Monika Ries、Lars Rose、Kai-Uwe Schöning、Thomas Weber、Andreas Kirschning

  DOI：10.1002/jlac.199719971015

  日期：1997.10

  addition, the iodine(III)-mediated oxidation process has been studied by in situ NMR spectroscopy of lyxo-configured glycals 14a,b. Intermediate alkylphenyliodonium species 19b,d and 2-enoyranosides 16a and 20a have been characterized by their NMR signals. These data support a plausible mechanism that is initiated by electrophilic attack of the iodine(III) reagent on the electron-rich enol ether double bond

  提出了充分证明的高价碘介导的糖基烯丙基氧化导致2,3-二氢-4 H-吡喃-4-酮的机理的研究。显着的特征是分离环-缩合副产物6和7，它们是由过O-苄基化的缩醛4氧化而产生的，以及表征由碳水化合物构筑的碳水化合物衍生的四氢糠醛12a和13a。依赖的氧化糖9a和10b。此外，还通过lyxo的原位NMR光谱研究了碘（III）介导的氧化过程。构型的糖基14a，b。中间烷基苯基碘鎓物质19b，d和2-烯吡喃糖苷16a和20a已通过其NMR信号表征。这些数据支持了一种合理的机理，该机理是由碘（III）试剂对糖基的富电子烯醇醚双键的亲电攻击引发的。接着是断开与碳水化合物结合的碘有关的β，γ键，随后还原性消除碘苯。因此，取决于所采用的糖基，可以形成多种多样的氧化产物。
• One-Step TEMPO-Catalyzed and Water-Mediated Stereoselective Conversion of Glycals into 2-Azido-2-deoxysugars with a PIFA–Trimethylsilyl Azide Reagent System
  作者：Ande Chennaiah、Yashwant D. Vankar

  DOI：10.1021/acs.orglett.8b00814

  日期：2018.5.4

  An unprecedented water-mediated and TEMPO-catalyzed, one-step, highly regiospecific and stereoselective functionalization of glycals to 2-azido-2-deoxysugars has been developed using a PIFA-Me3SiN3 reagent system in the presence of Bu4NHSO4 as a phase-transfer catalyst. The method is metal-free, proceeds under mild reaction conditions, and tolerates a variety of protecting groups. Using this method, the synthesis of an important trisaccharide unit bound by the monoclonal anti-I Ma antibody has also been demonstrated.
• Oxidation of Fully Protected Glycals by Hypervalent Iodine Reagents
  作者：Andreas Kirschning

  DOI：10.1021/jo00110a028

  日期：1995.3

  A new application of organoiodine(III) is presented. Fully protected glycals are directly converted into 2,3-dihydro-4H-pyran-4-ones by [hydroxy(tosyloxy)iodo]benzene (PhI(OH)OTs, 1). The detailed study reveals that this conversion is independent of the relative stereochemistry as well as the nature of protection on the pyran ring. 3-O-Silyl groups are most smoothly converted into the keto group giving 2,3-dihydro-4H-pyran-4-ones in yields up to 74%. In contrast, 4,6-di-O-acetyl-3-deoxyglucal (19) affords the rearranged oxidation product 32. Both observations can be reconciled by the proposed mechanism.
• Mereyala, Hari Babu; Venkataramanaiah, Kanamarlapudi C, Journal of Chemical Research, Miniprint, 1991, # 8, p. 1953 - 1966
  作者：Mereyala, Hari Babu、Venkataramanaiah, Kanamarlapudi C

  DOI：——

  日期：——