(+)-2,3-O-benzylidene-D-threitol | 35572-34-0

• 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: (+)-2,3-O-benzylidene-D-threitol
• 英文别名: (-)-2,3-o-Benzylidene-l-threitol；[(4S,5S)-5-(hydroxymethyl)-2-phenyl-1,3-dioxolan-4-yl]methanol
• CAS: 35572-34-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: AEJRVTSEJAYBNR-UWVGGRQHSA-N

物化性质

• 熔点：
  72-74 °C(lit.)
• 沸点：
  309.75°C (rough estimate)
• 密度：
  1.1922 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2932999099

SDS

Name:	(-)-2,3-O-Benzylidene-(L)-Threitol, 98% Material Safety Data Sheet
Synonym:	(4S,5S)-(-)-2-Phenyl-1,3-Dioxolane-4,5-Dimethanol.
CAS:	35572-34-0

Section 1 - Chemical Product MSDS Name: (-)-2,3-O-Benzylidene-(L)-Threitol, 98% Material Safety Data Sheet
Synonym: (4S,5S)-(-)-2-Phenyl-1,3-Dioxolane-4,5-Dimethanol.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
35572-34-0	(-)-2,3-O-Benzylidene-(L)-Threitol	98%	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.
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:

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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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 35572-34-0: 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 minimize contact with skin.
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: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 70.00 - 72.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H14O4
Molecular Weight: 210.23

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 35572-34-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(-)-2,3-O-Benzylidene-(L)-Threitol - 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# 35572-34-0: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 35572-34-0 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 35572-34-0 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 9/02/1997 Revision #4 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (+)-2,3-O-benzylidene-D-threitol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到1,3-二氧戊环-2-苯基-4,5-二苄溴
  参考文献：
  名称：

  咪唑基手性离子液体的合成与应用

  摘要：

  的含有咪唑核和手性中心的手性离子液体的合成ñ -取代基被报告。[（2小号，3小号）-2,3- Dihydroxybutane -1,4-双（3-丁基咪唑）] - [双（三氟甲磺酰）酰胺] 2和[（4-小号，5小号）-2-苯基-1- 1,3-二氧戊环-4,5-二（1-甲基咪唑）] - [双（三氟甲磺酰）酰胺] 2在迈克尔加成丙二酸酯的查耳酮向诱导对映选择性。

  DOI：

  10.1016/j.tet.2013.09.017
• 作为产物：
  描述：

  diethyl (4R,5R)-2-phenyl-1,3-dioxolane-4,5-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到(+)-2,3-O-benzylidene-D-threitol
  参考文献：
  名称：

  环孢菌素的合成。I.对映体纯的合成（2小号，3 - [R，4 - [R，6 ë）-3-羟基-4-甲基-2-甲氨基-6-辛烯酸从酒石酸起始†

  摘要：

  从R，R -（+）-酒石酸开始，报道了24步合成（2 S，3 R，4 R 6 E）-3-羟基-4-甲基-2-甲基-2-甲基氨基-6-辛烯酸。该新氨基酸存在于从真菌菌株Tolypocladium inflatum GAMS分离的环状十一肽环孢菌素A中。它的立体定向合成首次允许分离和表征先前报道为“ C-9-氨基酸”的新氨基酸[1]。

  DOI：

  10.1002/hlca.19830660742

文献信息

• Practical synthesis of 1-deoxy-d-xylulose and 1-deoxy-d-xylulose 5-phosphate allowing deuterium labelling
  作者：Odile Meyer、Jean-François Hoeffler、Catherine Grosdemange-Billiard、Michel Rohmer

  DOI：10.1016/j.tet.2004.10.016

  日期：2004.12

  are required for investigations on the mevalonate-independent 2-C-methyl-d-erythritol 4-phosphate pathway for isoprenoid biosynthesis in bacteria and chloroplasts of phototrophic eukaryotes and for the biosynthesis of vitamins B1 (thiamine diphosphate) and B6 (pyridoxol phosphate) in bacteria.

  优化的克级合成可以生产1-deoxy-d-木酮糖和1-deoxy-d-木酮糖5-磷酸，并可能在C-5处进行氘标记。此类底物是研究甲羟戊酸非依赖性2- C-甲基-d-赤藓糖醇4-磷酸途径用于光养性真核生物细菌和叶绿体中类异戊二烯生物合成以及维生素B 1（硫胺素二磷酸）和B 6（生物素）的生物合成所必需的。磷酸吡ido醇）。
• Selective Manipulation of Hydroxy Groups in (2<i>S</i>,3<i>S</i>)-Threitol
  作者：Seiichi Takano、Ayako Kurotaki、Yoshinori Sekiguchi、Shigeki Satoh、Michiyasu Hirama、Kunio Ogasawara

  DOI：10.1055/s-1986-31788

  日期：——

  Systematic transformation of diethyl (2R,3R)-tartrate into a number of protected or functionalized derivatives of threitol, which are important precursors for many natural products, is carried out employing reductive and oxidative cleavage reactions of benzylidene acetal bond.

  通过苯亚甲基缩醛键的还原和氧化断裂反应，系统性地将二乙基（2R,3R）-酒石酸转化为多种受保护或功能化的苏糖醇衍生物，这些衍生物是许多天然产物的重要前体。
• Mild and efficient method for the cleavage of benzylidene acetals by using erbium (iii) triflate
  作者：Antonio Procopio、Renato Dalpozzo、Antonio De Nino、Loredana Maiuolo、Monica Nardi、Giovanni Romeo

  DOI：10.1039/b511314h

  日期：——

  as new efficient Lewis acid catalyst in a mild deprotection protocol of benzylidene derivatives. In a modified procedure, where acetic anhydride is used as the reaction solvent, the simultaneous cleavage of the benzylidene acetal and the peracetylation of the substrates is obtained in quantitative yields and very short reaction times.

  在亚苄基衍生物的温和脱保护方案中，提出了Er（OTf）3作为新型有效的路易斯酸催化剂。在改进的方法中，其中使用乙酸酐作为反应溶剂，可以定量收率和非常短的反应时间实现亚苄基乙缩醛的同时裂解和底物的过乙酰化。
• Method for the total synthesis of cyclosporins, novel cyclosporins and
  申请人：Sandoz Ltd.

  公开号：US04396542A1

  公开（公告）日：1983-08-02

  A method for the total synthesis of cyclosporins, in particular Cyclosporin A, cyclosporins produced in accordance with the method of the invention and novel intermediates, in particular novel [1S, 2R, 3R]- and [1R, 2S, 3S]-1-nitrilo-1-carbonyl-3-methyl-2-oxy-heptanes and -hept-5-enes, employed in the method of the invention.

  一种用于环孢霉素的全合成的方法，特别是环孢霉素A，根据该发明方法生产的环孢霉素以及新型中间体，特别是新型[1S, 2R, 3R]-和[1R, 2S, 3S]-1-硝基-1-羧基-3-甲基-2-氧基-庚烷和-庚-5-烯，在该发明方法中使用。
• Synthesis of Cyclosporine. I. Synthesis of enantiomerically pure (2S,3R,4R,6E)-3-hydroxy -4-methyl-2-methylamino-6-octenoic acid starting from tartaric acid
  作者：Roland M. Wenger

  DOI：10.1002/hlca.19830660742

  日期：1983.11.2

  Starting from R,R-(+)-tartaric acid, the synthesis of (2S,3R,4R6E)-3-hydroxy -4-methyl-2-methylamino-6-octenoic acid in 24 steps is reported. This novel amino acid is found in the cyclic undecapeptide cyclosporin A, isolated from the fungal strain Tolypocladium inflatumGAMS. Its stereospecific synthesis allowed, for the first time, the isolation and characterization of the new amino acid previously

  从R，R -（+）-酒石酸开始，报道了24步合成（2 S，3 R，4 R 6 E）-3-羟基-4-甲基-2-甲基-2-甲基氨基-6-辛烯酸。该新氨基酸存在于从真菌菌株Tolypocladium inflatum GAMS分离的环状十一肽环孢菌素A中。它的立体定向合成首次允许分离和表征先前报道为“ C-9-氨基酸”的新氨基酸[1]。