2-脱氧-L-核糖 | 18546-37-7

• 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: 2-脱氧-L-核糖
• 英文名称: 2-deoxy-L-ribose
• 英文别名: 2-deoxy-L-erythro-pentose；L-2-deoxyribose；L-deoxyribose；L-erythro-2-deoxy-pentose；L-erythro-3,4,5-Trihydroxy-valeraldehyd；L-erythro-2-Desoxy-pentose；(3R,4S)-3,4,5-trihydroxypentanal
• CAS: 18546-37-7
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: ASJSAQIRZKANQN-UHNVWZDZSA-N

物化性质

• 熔点：
  69-72°C
• 比旋光度：
  57 º (c=0.9 H2O after 24h)
• 沸点：
  167.23°C (rough estimate)
• 密度：
  1.0590 (rough estimate)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn,Xi
• 安全说明：
  S24/25
• 危险类别码：
  R20/21/22
• 海关编码：
  2940000000
• 危险品运输编号：
  NONH for all modes of transport
• WGK Germany：
  3
• RTECS号：
  SB7230000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	2-Deoxy-L-Ribose Material Safety Data Sheet
Synonym:	None Known
CAS:	18546-37-7

Section 1 - Chemical Product MSDS Name:2-Deoxy-L-Ribose Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
18546-37-7	2-Deoxy-L-Ribose	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.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. 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# 18546-37-7: 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: Solid
Color: white - yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 69-72 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: Soluble.
Specific Gravity/Density:
Molecular Formula: C5H10O4
Molecular Weight: 134.13

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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:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 18546-37-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Deoxy-L-Ribose - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
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# 18546-37-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 18546-37-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 18546-37-7 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

制备方法与用途

简介

2-脱氧-L-核糖是一种白色或类白色的粉末，可溶于水和吡啶，微溶于乙醇。

用途

2-脱氧-L-核糖常用于生化研究。

反应信息

• 作为反应物：
  描述：

  2-脱氧-L-核糖 在 Raney-Ni (W-2) 盐酸 、 四溴化碳 、 三苯基膦 作用下， 以 乙醇 、 水 为溶剂， 反应 14.92h， 生成 (2R,3R)-(-)-1-bromo-erythro-pentane-2,3-diol
  参考文献：
  名称：

  Yusufoglu, Ayse; Antons, Stefan; Scharf, Hans-Dieter, Liebigs Annalen der Chemie, 1986, # 6, p. 1119 - 1123

  摘要：

  DOI：
• 作为产物：
  描述：

  1-t-butoxy-2-deoxy-L-ribose 在 甲苯 、 2-脱氧-L-核糖 、 L-anilide 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 2-脱氧-L-核糖
  参考文献：
  名称：

  PREPARATION METHOD OF 2-DEOXY-L-RIBOSE

  摘要：

  本发明公开了一种制备以下式I所示的2-脱氧-L-核糖的方法。该制备方法包括以下步骤：在酸的存在下，用醇溶剂处理L-阿拉伯糖以制备1-烷氧基-L-阿拉伯吡喃糖；让制备好的1-烷氧基-L-阿拉伯吡喃糖与酰氯反应，以制备1-烷氧基-2,3,4-三酰基-L-阿拉伯吡喃糖；溴化制备好的1-烷氧基-2,3,4-三酰基-L-阿拉伯吡喃糖的烷氧基，以制备1-溴基-2,3,4-三酰基化合物；在乙酸乙酯和有机碱的存在下，让制备好的化合物与锌反应，以制备葡萄糖醛；在酸的存在下，用醇溶剂处理葡萄糖醛，以制备1-烷氧基-2-脱氧-3,4-二酰基-L-核糖吡喃糖；用碱处理制备好的1-烷氧基-2-脱氧-3,4-二酰基-L-核糖吡喃糖，以制备1-烷氧基-2-脱氧-L-核糖吡喃糖；在酸催化剂的存在下，水解制备好的1-烷氧基-2-脱氧-L-核糖吡喃糖。

  公开号：

  US20090292117A1
• 作为试剂：
  描述：

  1-t-butoxy-2-deoxy-L-ribose 在 甲苯 、 2-脱氧-L-核糖 、 L-anilide 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 2-脱氧-L-核糖
  参考文献：
  名称：

  Preparation method of 2-deoxy-L-ribose

  摘要：

  公开了一种制备以下化学式I所表示的2-脱氧-L-核糖的方法。该制备方法包括以下步骤：在酸的存在下，用醇溶剂处理L-阿拉伯糖，制备1-烷氧基-L-阿拉伯吡喃糖；使制备的1-烷氧基-L-阿拉伯吡喃糖与酰氯反应，制备1-烷氧基-2,3,4-三酰基-L-阿拉伯吡喃糖；溴化制备的1-烷氧基-2,3,4-三酰基-L-阿拉伯吡喃糖的烷氧基，制备1-溴-2,3,4-三酰基化合物；在乙酸乙酯和有机碱的存在下，使制备的化合物与锌反应，制备葡萄糖缩醛；在酸的存在下，用醇溶剂处理葡萄糖缩醛，制备1-烷氧基-2-脱氧-3,4-二酰基-L-核糖吡喃糖；用碱处理制备的1-烷氧基-2-脱氧-3,4-二酰基-L-核糖吡喃糖，制备1-烷氧基-2-脱氧-L-核糖吡喃糖；在酸催化剂的存在下，水解制备的1-烷氧基-2-脱氧-L-核糖吡喃糖。

  公开号：

  US08114987B2

文献信息

• Effect of carbon chain length on catalytic C O bond cleavage of polyols over Rh-ReOx/ZrO2 in aqueous phase
  作者：Achraf Sadier、Noémie Perret、Denilson Da Silva Perez、Michèle Besson、Catherine Pinel

  DOI：10.1016/j.apcata.2019.117213

  日期：2019.9

  -tetraols, -triols, -diols, and hexanols) is achievable by hydrogenolysis of erythritol, xylitol, and sorbitol over supported-bimetallic Rh-ReOx (Re/Rh molar ratio 0.5) catalyst, respectively. After validation of the analytical methodology, the effect of some reaction parameters was studied. In addition to CO bond cleavage by hydrogenolysis, these polyols can undergo parallel reactions such as epimerization

  线性脱氧的C4（丁三醇，-二醇和丁醇），C5（戊四醇，-三醇，-二醇和戊醇）和C6产品（己烷五醇，-四醇，-三醇，-二醇和己醇）的生产可以实现赤藓糖醇，木糖醇和山梨糖醇分别在负载型双金属Rh-ReO x（Re / Rh摩尔比0.5）催化剂上进行氢解。在验证了分析方法之后，研究了一些反应参数的影响。除了通过氢解裂解C O键外，这些多元醇还可以进行平行反应，例如差向异构化，循环脱水和CC键裂解。线性脱氧C4，C5和C6产品每个家族的时间进程证实，不同类别的脱氧产品的出现顺序遵循多重顺序的脱氧途径。在高压下，在3.7wt。％Rh-3.5wt。％ReO x / ZrO 2催化剂存在下，对线性脱氧的C4，C5和C6产物混合物的最高选择性在80％的转化率下是有利的（54–71％ 80 bar下）在200°C下。
• Synthesis of beta-L-2'-deoxy nucleosides
  申请人：Storer Richard

  公开号：US20050059632A1

  公开（公告）日：2005-03-17

  An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro- 1 -furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  提供了一种改进的2'-改性核苷和2'-脱氧核苷的制备工艺，例如，β-L-2'-脱氧胸苷（LdT）。特别是，改进的工艺针对的是2'-脱氧核苷的合成，该合成可能使用不同的起始材料，但都通过氯糖中间体或通过2,2'-脱水-1-呋喃糖核苷中间体进行。当使用2,2'-脱水-1-呋喃糖碱基中间体时，会采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚），它们能引起分子内位移反应，并形成所需核苷产品的高收率。本发明的一种替代工艺使用2,2'-脱水-1-呋喃糖碱基中间体而不使用隔离剂，也能以高收率获得2'-脱氧核苷。根据本发明制成的化合物可以作为制备其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• Phormidolides B and C, Cytotoxic Agents from the Sea: Enantioselective Synthesis of the Macrocyclic Core
  作者：Adriana Lorente、Alejandro Gil、Rogelio Fernández、Carmen Cuevas、Fernando Albericio、Mercedes Álvarez

  DOI：10.1002/chem.201404341

  日期：2015.1.2

  New cytotoxic polyketide macrolides named phormidolides B and C were isolated from a marine sponge of the Petrosiidae family collected off the coast of Pemba (Tanzania). The isolation, structure elucidation, and enantioselective synthesis of three diastereomers of the macrocyclic core is described herein. The described synthetic methodology started from 2‐deoxy‐D‐ribose or 2‐deoxy‐L‐ribose and afforded

  新的细胞毒性聚酮类大环内酯类化合物称为隐吸虫B和C，是从奔巴（坦桑尼亚）沿海采集的Petrosiidae科海洋海绵中分离出来的。本文描述了大环核心的三种非对映异构体的分离，结构阐明和对映选择性合成。所描述的合成方法从2-脱氧-D-核糖或2-脱氧-L-核糖开始，提供了所需的具有高对映体纯度的大环化合物。合成的关键步骤是使用Julia-Kocienski烯烃形成Z-三取代双键。合成方法的多功能性可以通过改变起始材料或手性诱导剂来提供其他对映纯大环化合物的途径。
• Complementary and Stereodivergent Approaches to the Synthesis of 5-Hydroxy- and 4,5-Dihydroxypipecolic Acids from Enantiopure Hydroxylated Lactams
  作者：Dina Scarpi、Laura Bartali、Andrea Casini、Ernesto G. Occhiato

  DOI：10.1002/ejoc.201201429

  日期：2013.3

  describe two complementary and stereodivergent routes, from commercially available and inexpensive starting materials, for the synthesis of 4,5-dihydroxy- and 5-hydroxypipecolic acids based on the chemistry of lactam-derived enol phosphates. The synthesis of the 4,5-cis-4,5-dihydroxypipecolic acids required the preparation from 2-deoxy-D- and -L-ribose of the enantiopure cis-(4S,5R)- and -(4R,5S)-4

  我们描述了两种互补和立体发散的路线，从市售和廉价的起始材料中，基于内酰胺衍生的烯醇磷酸酯的化学合成 4,5-二羟基和 5-羟基哌啶酸。4,5-顺式-4,5-二羟基哌啶酸的合成需要从对映体纯顺式-(4S,5R)-和-(4R,5S)-的2-脱氧-D-和-L-核糖制备分别为 4,5-二羟基-δ-戊内酰胺。这些新的手性合成子可用于合成其他天然产物。关键步骤是由这些内酰胺生成的烯醇磷酸酯的 Pd 催化甲氧基羰基化反应。该反应提供的烯氨基甲酸酯很容易通过立体选择性还原转化为目标化合物。4,5-反式-4,5-二羟基哌可酸的合成，以及 5-羟基哌啶酸，由已知的 (S)-5-羟基-δ-戊内酰胺衍生物实现，对于二羟基化合物，需要对烯醇甲氧基羰基化获得的烯氨基甲酸酯进行高度立体选择性烯丙基溴化反应磷酸盐。从 2-脱氧-L-核糖制备顺式-4,5-二羟基-δ-戊内酰胺的 (4R,5S) 对映体，同时可以制备 (R)-5-羟基-δ-戊内酰胺来自
• DETERMINATION OF CONFIGURATION OF MONOSACCHARIDES BY HPLC ON DIASTEREOISOMERIC 1-DEOXY-1-(<i>N</i>-ACETYL-α-METHYLBENZYLAMINO)ALDITOL ACETATES
  作者：Ryuichi Oshima、Ju Kumanotani

  DOI：10.1246/cl.1981.943

  日期：1981.7.5

  Acyclic diastereoisomers, 1-deoxy-1-(N-acetyl-α-methylbenzylamino)alditol acetates, are readily obtained by reductive amination of sugars with chiral α-methylbenzylamine in the presence of sodium cyanoborohydride. Ten pairs of enantiomers of common monosaccharides are resolved by an adsorption HPLC on the diastereoisomers.

  无环非对映异构体，1-脱氧-1-（N-乙酰基-α-甲基苄氨基）醛醇乙酸酯，在氰基硼氢化钠的存在下，通过手性α-甲基苄胺对糖的还原胺化很容易获得。十对常见单糖的对映异构体通过非对映异构体上的吸附 HPLC 进行拆分。