4-甲氧苯基2,6-二-O-苄基-β-D-吡喃葡萄糖苷 | 159922-50-6

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲氧苯基2,6-二-O-苄基-β-D-吡喃葡萄糖苷
• 中文别名: 4-甲氧苯基-2,6-二-O-苄基-Β-D-吡喃半乳糖苷；4-甲氧苯基2,6-二-O-苄基-Beta-D-吡喃半乳糖苷
• 英文名称: 4-methoxyphenyl 2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: p-methoxyphenyl 2,6-di-O-benzyl-β-D-galactopyranoside；4-Methoxyphenyl 2,6-Di-O-benzyl-beta-D-galactopyranoside；(2R,3R,4S,5R,6S)-6-(4-methoxyphenoxy)-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 159922-50-6
• 化学式: C₂₇H₃₀O₇
• 分子量: 466.531
• InChiKey: ZNONEMGWLHXQDN-LXSUACKSSA-N

物化性质

• 熔点：
  113 °C
• 沸点：
  641.1±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 溶解度：
  微溶于在氯仿中

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 海关编码：
  29389090
• 储存条件：
  保存方法：冰箱内

SDS

4-Methoxyphenyl 2,6-Di-O-benzyl-β-D- Revision number: 5
galactopyranoside
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
4-Methoxyphenyl 2,6-Di-O-benzyl-β-D-galactopyranoside
Product name:


Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
Not classified
PHYSICAL HAZARDS
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
None
Pictograms or hazard symbols
Signal word No signal word
None
Hazard statements
Precautionary statements: None

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4-Methoxyphenyl 2,6-Di-O-benzyl-β-D-galactopyranoside
Percent: >98.0%(LC)
CAS Number: 159922-50-6
Chemical Formula: C27H30O7

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
4-Methoxyphenyl 2,6-Di-O-benzyl-β-D-
galactopyranoside

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Section 5. FIRE-FIGHTING MEASURES
When extinguishing fire, be sure to wear personal protective equipment.
Special protective
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a freezer.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive
Comply with laws.
Packaging material:

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: White - Very pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:113°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
No data available
Relative density:
Solubility(ies):
[Water] No data available
[Other solvents]
Slightly soluble: Chloroform

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
4-Methoxyphenyl 2,6-Di-O-benzyl-β-D-
galactopyranoside

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Section 10. STABILITY AND REACTIVITY
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Not listed
UN-No:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
4-Methoxyphenyl 2,6-Di-O-benzyl-β-D-
galactopyranoside

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

半乳糖（糖科学）

反应信息

• 作为反应物：
  描述：

  4-甲氧苯基2,6-二-O-苄基-β-D-吡喃葡萄糖苷 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 p-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  使用5,7-O-二叔丁基亚甲硅烷基保护的Kdo乙基硫代糖苷供体立体选择性合成α-3-脱氧-D-甘露聚糖-八-磺酸（α-Kdo）糖苷

  摘要：

  对于α-KDO糖苷键合成中的有效方法已被开发5,7- ö二-叔-butylsilylene（DTBS）保护的KDO乙基硫代糖苷作为糖供体。该方法允许使用广泛的受体，从而提供生物学上重要的Kdo糖苷，具有良好的化学产率和完全的α选择性。两种含α-Kdo的寡糖的简洁制备已证明了正交保护的Kdo供体的合成效用。

  DOI：

  10.1002/anie.201505176
• 作为产物：
  描述：

  4-甲氧苯基2,6-二-O-苄基-3,4-O-异亚丙基-β-D-吡喃半乳糖苷 在 水 、 溶剂黄146 作用下， 反应 2.0h， 以303 mg的产率得到4-甲氧苯基2,6-二-O-苄基-β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  硫酸化鞘糖脂 SM1a 的全合成，一种人类上皮癌抗原

  摘要：

  首次实现了一种高效、实用的全合成硫酸化神经节苷脂SM1a，一种在哺乳动物肾脏中鉴定的人类上皮癌抗原。SM1a的特征序列，β-D-Galp-(13)-β-D-NHAcGalp-(14)-β-D-(3-O-硫酸盐)-Galp-(14)-β-D-Glcp-神经酰胺是通过 [3+2] 会聚方法组装的。一个关键的三糖构建块由含有潜在硫酸化位点的新半乳糖受体 7、GalNHTroc 供体 6 和半乳糖供体 4 形成。环状葡萄糖神经酰胺与三糖三氯乙酰亚胺 2 糖基化，以良好的收率得到受保护的神经节苷脂骨架。在 Gal 残基的 3-OH 处选择性磺化，然后全局脱保护，得到目标分子 SM1a。

  DOI：

  10.1002/ejoc.201403296

文献信息

• 二環性ウロソン酸誘導体の製造方法およびウロソン酸誘導体の製造方法
  申请人：国立大学法人岐阜大学

  公开号：JP2020158489A

  公开（公告）日：2020-10-01

  【課題】種々の基質（求核剤）に対してα選択性が特異的に高く、目的とするα体の二環性ウロソン酸誘導体およびウロソン酸誘導体を高い収率で得ることができる、二環性ウロソン酸誘導体の製造方法およびウロソン酸誘導体の製造方法を提供すること。【解決手段】二環性ウロソン酸誘導体の製造方法は、環状構造を有するウロソン酸類のＣ１位とＣ５位とが架橋基で架橋されることにより、β面が遮蔽された１，４−シス体の二環性ウロソン酸求電子剤と、求核剤とを反応させることにより、二環性ウロソン酸求電子剤のＣ２位に求核剤をα結合させ、二環性ウロソン酸誘導体を合成するα結合形成工程を有することを特徴とする。【選択図】なし

  对各种底物（亲核试剂）具有高度特异性的α选择性，能够以高收率获得所需的α体二环尿酸衍生物和尿酸衍生物，提供一种制备二环尿酸衍生物和尿酸衍生物的方法。制备二环尿酸衍生物的方法包括通过将尿酸类化合物的C1位和C5位通过桥联基桥联形成环状结构，使β面被屏蔽的1,4-顺式体的二环尿酸亲电试剂与亲核试剂反应，将亲核试剂与二环尿酸亲电试剂的C2位α连接，具有合成二环尿酸衍生物的α连接形成步骤。【选择图】无
• Silicon Fluorides for Acid-Base Catalysis in Glycosidations
  作者：Amit Kumar、Yiqun Geng、Richard R. Schmidt

  DOI：10.1002/adsc.201100933

  日期：2012.5.21

  Adduct formation between alcohols as glycosyl acceptors and phenylsilicon trifluoride (PhSiF3) as catalyst permits acid‐base‐atalyzed glycosidations with O‐glycosyl trichloroacetimidates as glycosyl donors. In this way, from various glycosyl donors and acceptors 1,2‐trans‐ and some 1,2‐cis‐glycosides could be obtained with high anomeric selectivity. A preference for an intramolecular bimolecular nucleophilic

  醇（作为糖基受体）与苯基三氟化硅（PhSiF 3）作为催化剂之间的加合物形成允许酸碱催化的糖基化反应，其中O-糖基三氯乙酰胺酸作为糖基供体。这样，可以从各种糖基供体和受体以高异头异构体选择性获得1,2-反式和一些1,2-顺式-糖苷。结果显示，偏爱分子内双分子亲核取代（S N 2型）反应过程，伴有供体和受体激活。
• Silylene/Oxazolidinone Double-Locked Sialic Acid Building Blocks for Efficient Sialylation Reactions in Dichloromethane
  作者：Shinya Hanashima、Ken-ichi Sato、Yukishige Ito、Yoshiki Yamaguchi

  DOI：10.1002/ejoc.200900543

  日期：2009.9

  We describe efficient sialylation reactions in CH2Cl2 with the use of silylene/oxazolidinone double-locked sialic acid building blocks. The building blocks were synthesized from 4,5-oxazolidinone-protected phenylthiosialoside. In sialylation reactions towards primary and relatively reactive secondary hydroxy groups on the galactosides, the double-locked building blocks provided desired coupling products

  我们描述了使用亚甲硅烷基/恶唑烷酮双锁唾液酸构建块在 CH2Cl2 中的有效唾液酸化反应。构建块由 4,5-恶唑烷酮保护的苯基硫代唾液酸合成。在针对半乳糖苷上的伯羟基和相对反应性仲羟基的唾液酸化反应中，双锁结构单元以良好的收率和优异的α-选择性提供了所需的偶联产物。在与半乳糖苷的 C3-OH 的唾液酸化反应中，与使用恶唑烷酮锁定结构单元获得的结果相比，双锁定结构单元表现出明显更好的 α 选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions
  作者：Abhishek Santra、Goutam Guchhait、Anup Kumar Misra

  DOI：10.1039/c1gc15122c

  日期：——

  fast and efficient acylation of carbohydrate derivatives and free sugars using a stoichiometric quantity of acylating agents in the presence of sulfamic acid, an environmentally benign catalyst, under organic solvent-free conditions is reported. Excellent yields in the selective acylation and sulfation of carbohydrate derivatives have also been achieved using sulfamic acid as the catalyst. The reaction

  快速高效 酰化 的 碳水化合物衍生物 在存在以下条件下，使用化学计量的酰化剂制备游离糖和游离糖 氨基磺酸，对环境无害 催化剂，在有机 溶剂-无条件的报道。选择性的酰化和硫酸化硫酸具有优异的收率碳水化合物衍生物 也已经通过使用 氨基磺酸 作为 催化剂。反应速度快，收率优异。
• A Highly α-Stereoselective Sialylation Method Using 4-<i>O</i> -4-Nitropicoloyl Thiosialoside Donor
  作者：Dong-Mei Liu、Hong-Ling Wang、Jin-Cai Lei、Xian-Yang Zhou、Jin-Song Yang

  DOI：10.1002/ejoc.201901587

  日期：2020.2.7

  The sialic acid ethyl thioglycoside donor, bearing a 4‐nitropicoloyl moiety as the stereodirecting group at the C4 position, can successfully achieve highly α‐sialylation with various acceptors. The method has been extended to the stereocontrolled synthesis of the protected trisaccharide found in the repeating unit of serotype Ia Group B Streptococcus capsular polysaccharide.

  唾液酸乙基硫代糖苷供体，在C4位置带有一个4 －硝基香叶基作为立体定向基团，可以成功地实现与各种受体的高度α－唾液酸化。该方法已扩展到在血清型Ia B族链球菌荚膜多糖重复单元中发现的被保护的三糖的立体控制合成。