3,4-di-O-benzyl-L-rhamnal | 117249-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-di-O-benzyl-L-rhamnal
• 英文别名: (2S,3S,4S)-3,4-bis(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran；(2S,3S,4S)-2-methyl-3,4-bis(phenylmethoxy)-3,4-dihydro-2H-pyran
• CAS: 117249-17-9
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: QNLJVGMVNHDIKM-VDGAXYAQSA-N

物化性质

• 熔点：
  27-29 °C
• 沸点：
  434.2±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25

SDS

Name:	3 4-Di-O-benzyl-L-rhamnal Material Safety Data Sheet
Synonym:
CAS:	117249-17-9

Section 1 - Chemical Product MSDS Name:3 4-Di-O-benzyl-L-rhamnal Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
117249-17-9	3,4-Di-O-benzyl-L-rhamnal		unlisted

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

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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.

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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.

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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.
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.

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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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 117249-17-9: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 111 - 113 deg C
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: C20H22O3
Molecular Weight: 310.39

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials.
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# 117249-17-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Di-O-benzyl-L-rhamnal - 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# 117249-17-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 117249-17-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 117249-17-9 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：

  3,4-di-O-benzyl-L-rhamnal 在 水 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以99%的产率得到3,4-di-O-benzyl-2-deoxy-L-rhamnopyranose
  参考文献：
  名称：

  [EN] MACROCYCLIC PICOLINAMIDE COMPOUNDS WITH FUNGICIDAL ACTIVITY
  [FR] COMPOSÉS DE PICOLINAMIDE MACROCYCLIQUE PRÉSENTANT UNE ACTIVITÉ FONGICIDE

  摘要：

  本公开涉及式(I)的宏观环状吡啶酰胺及其作为杀菌剂的应用。

  公开号：

  WO2016109290A1
• 作为产物：
  描述：

  L-rhamnopyranose 在 吡啶 、 甲醇 、 sodium dihydrogenphosphate 、 氢溴酸 、 sodium 、 sodium hydride 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 3,4-di-O-benzyl-L-rhamnal
  参考文献：
  名称：

  通过温度和布朗斯台德酸度调节甲硅烷基保护鼠李的化学选择性：动力学控制的1,2-加成与热力学控制的重排

  摘要：

  已经揭示了醇对甲硅烷基保护的鼠类的酸度和温度依赖性的化学选择性糖基化作用。该反应在室温下以（±）-CSA作为催化剂经历1，2-加成途径，得到动力学控制的2-脱氧鼠李糖苷。相反，当将反应温度提高到85°C或使用CF 3 SO 3 H时，通过Ferrier重排仅形成热力学控制的2,3-不饱和鼠李糖苷。这种可调节的糖基化可以轻松，实用地获得2-脱氧和2,3-不饱和鼠李糖苷，并具有出色的收率和高α-立体选择性。

  DOI：

  10.1021/acs.orglett.9b00009

文献信息

• A New Method for the Stereoselective Synthesis of α- and β-Glycosylamines Using the Burgess Reagent
  作者：K. C. Nicolaou、Scott A. Snyder、Annie Z. Nalbandian、Deborah A. Longbottom

  DOI：10.1021/ja049293c

  日期：2004.5.1

  Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts. In this communication, we report an operationally simple method for the synthesis of both α- and β-glycosylamines using the Burgess reagent that overcomes

  尽管从生物学和医学的角度来看，糖基胺构成了一组重要的碳水化合物，但它们的合成方法通常缺乏底物的通用性和/或导致可变的立体选择性，尤其是在复杂的环境中。在这篇通讯中，我们报告了一种使用 Burgess 试剂合成 α- 和 β- 糖基胺的操作简单的方法，该方法以最少的合成步骤克服了许多这些限制。
• MACROCYCLIC PICOLINAMIDES AS FUNGICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：US20130296375A1

  公开（公告）日：2013-11-07

  The invention relates to macrocyclic picolinamides of Formula I and their use as fungicides.

  这项发明涉及式I的大环状吡啶甲酰胺及其作为杀菌剂的应用。
• Lewis acid/base pair as a catalytic system for α-stereoselective synthesis of 2-deoxyglycosides through the addition of alcohols to glycals
  作者：Chen Wang、Haijing Liang、Zhaojun Hang、Zhao-yan Wang、Qinjian Xie、Weihua Xue

  DOI：10.1016/j.tetlet.2020.152643

  日期：2020.12

  report describes the α-stereoselective addition of alcohols to glycals promoted by a cooperative Lewis acid/base pair catalytic system composed of B(C6F5)3 and tetrabutylammonium bromide (TBAB), which provides access to 2-deoxylglycosides in high yields. A mechanistic investigation supported by NMR analysis highlights the possible involvement of nucleophilic addition through boron-induced activation of

  该报告描述了由B（C 6 F 5）3和溴化四丁铵（TBAB）组成的路易斯酸/碱对催化催化体系促进的α-立体选择性醇加成糖，可高产率地获得2-脱氧糖苷。NMR分析支持的机理研究突显了在TBAB的帮助下，通过硼诱导的醇活化，亲核加成可能参与其中。这里讨论的协议具有高的立体选择性，温和的反应条件，廉价且稳定的催化剂以及广泛的底物范围。
• Stereoselective organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings
  作者：G. A. Bradshaw、A. C. Colgan、N. P. Allen、I. Pongener、M. B. Boland、Y. Ortin、E. M. McGarrigle

  DOI：10.1039/c8sc02788a

  日期：——

  Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%.

  硫尿嘧啶在载体负载量低至0.1 mol％时，催化与半乳糖醛糖苷的立体选择性糖基化。
• Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis
  作者：Gaoyuan Zhao、Ting Wang

  DOI：10.1002/anie.201800909

  日期：2018.5.22

  The direct, photoacid‐catalyzed synthesis of 2‐deoxyglycosides from glycals is reported. A series of phenol‐conjugated acridinium‐based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford

  据报道，由糖类直接，光酸催化合成了2-脱氧糖苷。与市售的酚催化剂曙红Y一起，合理设计，合成和研究了一系列基于酚共轭啶基的有机光酸。在这种光酸催化剂和光的存在下，合成糖被活化并与多种醇偶联以高收率和优异的α-选择性提供2-脱氧糖苷。