甲基-L-吡喃岩藻 | 65310-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基-L-吡喃岩藻
• 英文名称: methyl L-fucopyranoside
• 英文别名: (3S,4R,5S,6S)-2-Methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol；(3S,4R,5S,6S)-2-methoxy-6-methyloxane-3,4,5-triol
• CAS: 65310-00-1
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: OHWCAVRRXKJCRB-DVEMRHSHSA-N

物化性质

• 熔点：
  150-152°C
• 沸点：
  230.4°C (rough estimate)
• 密度：
  1.1571 (rough estimate)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）、水（微溶）
• 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)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2932999099
• 储存条件：
  存放于阴凉干燥处

SDS

Name:	Methyl-L-fucopyranoside Material Safety Data Sheet
Synonym:	None Known
CAS:	65310-00-1

Section 1 - Chemical Product MSDS Name:Methyl-L-fucopyranoside Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
65310-00-1	Methyl-L-fucopyranoside	ca. 100	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
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. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 65310-00-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Powder
Color: white
Odor: odorless
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: C7H14O5
Molecular Weight: 178.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 65310-00-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl-L-fucopyranoside - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 65310-00-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 65310-00-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 65310-00-1 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：

  甲基-L-吡喃岩藻 在 盐酸 、 溶剂黄146 、 potassium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 生成 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  针对多重耐药病原体：新洋葱伯克霍尔德菌的 BC2L-C 凝集素的第一代拮抗剂

  摘要：

  新洋葱伯克霍尔德菌等多重耐药病原体已成为医疗保健相关感染的危险因素，尤其是对于患有囊性纤维化或免疫功能低下病症的患者而言。与其他机会性革兰氏阴性细菌一样，这种病原体通过凝集素介导的粘附建立毒力和生物膜。特别是，超凝集素 BC2L -C 被认为在肺部感染期间将人类上皮细胞与新洋葱伯克氏菌交联。我们旨在获得能够抑制N之间相互作用的拟糖拮抗剂-BC2L-C (BC2L-C-Nt) 及其目标岩藻糖基化人寡糖的末端结构域。在之前的一项研究中，我们通过片段虚拟筛选进行鉴定，并验证了一小部分在岩藻糖结合位点附近结合 BC2L-C-Nt 的分子片段。在这里，我们报告了双功能C - 或N的合理设计和合成-岩藻糖苷，通过使用一组合理选择的接头将这些片段连接到岩藻糖苷核心而产生。从两个关键岩藻糖苷中间体开始的模块化路线用于合成，然后使用一系列技术（表面等离子体共振、等温滴定量热法、饱和转移差 NMR、差示扫描）评估新化合物作为

  DOI：

  10.1021/acschembio.2c00532
• 作为产物：
  描述：

  6-deoxy-L-galactose 在 Amberlite IR-120 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 甲基-L-吡喃岩藻
  参考文献：
  名称：

  抗生素支链霉素的 O-氨基甲酰基糖成分支链淀粉的合成

  摘要：

  直链淀粉的首次合成是一种强效广谱抗生素支链霉素的O-氨基甲酰基吡喃糖成分，已从 L-岩藻糖分 8 个步骤完成。关键的转化包括通过氧化/还原序列在 L-岩藻糖衍生物的 C 2 不对称中心进行立体化学反转，通过酸促进的环状原酸酯水解和四溴化钛区域选择性安装 3-乙酰氧基官能团。介导的倒数第二个糖苷中间体的水解。

  DOI：

  10.1016/j.tetlet.2022.153891

文献信息

• Tin-Mediated Regioselective Benzylation and Allylation of Polyols: Applicability of a Catalytic Approach Under Solvent-Free Conditions
  作者：Maddalena Giordano、Alfonso Iadonisi

  DOI：10.1021/jo402399n

  日期：2014.1.3

  The first catalytic version of the stannylene-mediated benzylation and allylation of polyols is reported. The methodology is based on a simple solvent-free protocol that significantly advances, in terms of both experimental ease and synthetic scope, the applicability of tin-promoted selective protections. The described approach is indeed endowed with a very large number of advantages over routine protocols:

  报道了由亚苯乙烯介导的多元醇的苄基化和烯丙基化的第一个催化形式。该方法基于简单的无溶剂方案，在实验简便性和合成范围方面，都大大提高了锡促进的选择性保护的适用性。与常规方案相比，所描述的方法确实具有许多优点：使用低催化负载量的廉价Bu 2SnO是避免使用溶剂的一步法工艺，是在空气中进行反应的最低要求的实验程序，缩短了反应时间，简化了后处理工艺，目标范围广，在许多情况下，收率均优于常规协议。另外，无催化溶剂的方法将亚锡烷基化学的范围扩展到了空前的应用领域，以还原糖和合成高苄基化的结构单元，而这些过程可以通过更苛刻的程序来获得。从概念的角度来看，所描述的结果表明，无溶剂条件可以帮助开发催化方法，否则该方法在溶液中无效。
• Patentiflorin A Analogs as Antiviral Agents
  申请人：Hong Kong Baptist University

  公开号：US20210060042A1

  公开（公告）日：2021-03-04

  The present disclosure relates to patentiflorin A analogs that are useful as antivirals, such as anti-HIV, anti-coronaviral, anti-Ebola viral, and anti-influenza viral agents and methods of use thereof.

  本公开涉及用作抗病毒药物的帕特尼氟林A类似物，例如抗HIV、抗冠状病毒、抗埃博拉病毒和抗流感病毒药物，以及它们的使用方法。
• Iodonium ion-assisted synthesis of tetrameric fragments corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovars II and IV
  作者：Korien Zegelaar-Jaarsveld、Howard I. Duynstee、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0040-4020(96)00034-8

  日期：1996.3

  The spacer-containing tetramers 3 and 4, derivatives of the phenolic glycolipids of Mycobacterium kansasii serovars II and IV were prepared by iodonium ion-mediated mannosylation of trimeric acceptor 4-[2-(benzyloxycarbonylamino)ethyl]phenyl (2) with ethyl 1-thio-d-mannopyranoside donors 7, 13, and 24. In addition, the glycosylating properties of donors 7, 13, 24, 29–31, each containing a different

  含间隔基的四聚体3和4，堪萨斯分枝杆菌血清型II和IV的酚糖脂衍生物是通过碘离子介导的三聚体受体4- [2-（苄氧基羰基氨基）乙基]苯基（2）与1-乙基的甘露糖基化反应制得的。硫代d-D-吡喃甘露糖苷供体7，13，和24。此外，供体的糖基化特性7，13，24，29-31，每个包含一个不同的保护基团在2位，通过用模型受体执行缩合检查18（L）和其对映体18（d）。
• An improved method for the preparation of standards for glycosyl-linkage analysis of complex carbohydrates
  作者：Steven H. Doares、Peter Albersheim、Alan G. Darvill

  DOI：10.1016/0008-6215(91)80131-6

  日期：1991.3

  We describe herein a simple procedure that yields a mixture of all possible partially O-methylated, partially O-acetylated alditols that can be formed from a given methyl glycoside

  我们在本文中描述了一种简单的程序，该程序可产生可以由给定的甲基糖苷形成的所有可能的部分O-甲基化，部分O-乙酰化的糖醇的混合物
• PROCESS FOR PRODUCING 2'-O-FUCOSYLLACTOSE
  申请人：BASF SE

  公开号：US20210130384A1

  公开（公告）日：2021-05-06

  The present invention relates to a method for preparing 2′-O-fucosyllactose, the intermediates obtainable by this method and the use of these intermediates. The preparation comprises the reaction of a protected fucose of the general formula (I) with a tri(C 1 -C 6 -alkyl)silyl iodide to give a protected 1-iodofucose followed by the reaction of the protected 1-iodofucose with a compound of the general formula (II), in the presence of at least one base and deprotecting the resulting coupling product to afford 2′-O-fucosyllactose. In this context, the variables are each defined as follows: R a and R b are the same or different and are —C(═O)—C 1 -C 6 -alkyl, or —C(═O)-phenyl, wherein said phenyl is unsubstituted or optionally has 1 to 5 substituents, or R a and R b together are a radical —(C═O)— or a substituted methylene radical —C(R d R e )—, R c is a radical R Si or is benzyl, wherein said benzyl is unsubstituted or optionally has 1, 2 or 3 substituents, R Si is a radical of the formula SiR f R g R h , where R f , R g and R h are the same or different and are C 1 -C 8 -alkyl for example, R 1 is a radical —C(═O)—R 11 or a radical SiR 12 R 13 R 14 R 2 are the same or different and are C 1 -C 8 -alkyl for example; R 3 are the same or different and are for example C 1 -C 8 -alkyl or both radicals R 3 together form a linear C 1 -C 4 -alkenyl, which is unsubstituted or has 1 to 6 methyl groups as substituents.

  本发明涉及一种制备2'-O-岩藻糖乳的方法，以及通过该方法可获得的中间体和这些中间体的用途。该制备包括将一般式（I）的保护岩藻糖与三（C1-C6-烷基）硅基碘反应，得到保护1-碘岩藻糖，然后将保护1-碘岩藻糖与一般式（II）的化合物在至少一种碱的存在下反应，并去保护所得的偶联产物以得到2'-O-岩藻糖。在这种情况下，变量的定义如下：Ra和Rb相同或不同，为—C(═O)—C1-C6-烷基，或—C(═O)-苯基，其中所述苯基未取代或可选地具有1至5个取代基，或者Ra和Rb一起是一个基团—(C═O)—或一个取代亚甲基基团—C(RdRe)—，Rc是基团RSi或苄基，其中所述苄基未取代或可选地具有1、2或3个取代基，RSi是具有式SiRfRgRh的基团，其中Rf、Rg和Rh相同或不同，为C1-C8-烷基，例如，R1是基团—C(═O)—R11或基团SiR12R13R14，R2相同或不同，为C1-C8-烷基，例如，R3相同或不同，例如为C1-C8-烷基，或两个基团R3一起形成未取代或具有1至6个甲基基团作为取代基的线性C1-C4-烯基。