(1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯 | 98760-08-8

• 物质功能分类: 有机原料 - 氨基化合物 - 含氧基氨基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯
• 中文别名: (2R,3S)-1,2-环氧基-3-(Boc-氨基)-4-苯基丁烷；(2R,3S)-1,2-环氧-3-叔丁氧羰基氨基-4-苯基丁烷；[(1S)-1-(2R)-环氧乙烷-2-苯基乙基]-氨基甲酸-(1,1-二甲基)乙酯；(2R,3S)-环氧乙基-1-苯乙基氨基甲酸叔丁酯；(2R,3S)-3-(叔丁氧羰基氨基)-4-苯基-1,2-环氧丁烷
• 英文名称: (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
• 英文别名: (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane；tert-butyl N-[(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl]carbamate
• CAS: 98760-08-8
• 化学式: C₁₅H₂₁NO₃
• mdl: MFCD00671705
• 分子量: 263.337
• InChiKey: NVPOUMXZERMIJK-STQMWFEESA-N

物化性质

• 熔点：
  50-52°C
• 沸点：
  398.8±25.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (2R,3S)-3-(t-BOC)amino-1,2-epoxy-4-phenylbutane
Synonyms: (2R,3S)-(+)-3-(N-Boc-amino)-1-oxirane-4-phenylbutane

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: (2R,3S)-3-(t-BOC)amino-1,2-epoxy-4-phenylbutane
CAS number: 98760-08-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C15H21NO3
Molecular weight: 263.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

((2R,3S)-1,2-环氧-3-叔丁氧羰基氨基-4-苯基丁烷) 是一种粉末状物质，主要用作阿扎那韦的中间体。

反应信息

• 作为反应物：
  描述：

  (1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯 在 盐酸 、 氢气 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 、 异丙醇 为溶剂， 生成 地瑞那韦乙醇盐
  参考文献：
  名称：

  An improved and robust scale-up process aided with identification and control of critical process impurities in darunavir ethanolate

  摘要：

  开发了一种强健且安全的工业过程，包括五个分离和干燥步骤，用于广泛处方的抗 HIV 药物达鲁那韦乙酸盐（darunavir ethanolate）2。该过程的一大显著特点是开发了能够高效合成多公斤量达鲁那韦乙酸盐的程序，并提供了通过工厂规模制备的过程示范。在此过程中，达鲁那韦分子以总体化学产率超过 70% 和纯度超过 99.8% 的水平制备，并且没有涉及任何纯化程序，所有可能的工艺杂质均低于所需限度（不超过 0.08%），这些杂质均已被分离、合成和表征。该开发的过程完全强健、效率极高，并且在公斤级制备上得到了验证。

  DOI：

  10.1007/s11164-019-03948-4
• 作为产物：
  描述：

  N-乙酰-L-苯丙氨酸 在 三聚甲醛 、 四氯化碳 、 sodium 、 sodium hydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 13.0h， 生成 (1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯
  参考文献：
  名称：

  一种安普那韦中间体的制备方法

  摘要：

  本发明涉及一种抗艾滋病药物安普那韦中间体的合成方法，具体涉及一种(2R,3S)-1,2-环氧基-3-(叔丁氧羰基氨基)-4-苯基丁烷的合成方法，包括以下步骤：以L-苯丙氨酸为原料，与乙酸酐反应生成N-乙酰-L-苯丙氨酸，然后经Mannich反应，Appel反应，烯烃环氧化作用得到该中间体，该方法制备(2R,3S)-1,2-环氧基-3-(叔丁氧羰基氨基)-4-苯基丁烷路线合理，操作性强，收率高，易于实现工业化生产。

  公开号：

  CN105348224A
• 作为试剂：
  描述：

  (1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯 、 3-Methyl-N-[(phenylmethoxy)carbonyl]-L-valine 2-[[4-(2-pyridinyl)phenyl]methyl]hydrazide 在 (1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯 作用下， 生成 12-Oxa-2,5,6,10-tetraazatetradecanoic acid, 3-(1,1-dimethylethyl)-8-hydroxy-13,13-dimethyl-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-, phenylmethyl ester, (3S,8S,9S)-
  参考文献：
  名称：

  WO2008065490A2

  摘要：

  公开号：

文献信息

• HIV protease inhibiting compounds
  申请人：Flentge Charles A.

  公开号：US20110003827A1

  公开（公告）日：2011-01-06

  A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

  公开了一种具有以下公式的化合物，作为HIV蛋白酶抑制剂。还公开了抑制HIV感染的方法和组合物。
• 5-amino-4-hydroxyhexanoic acid derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US05643878A1

  公开（公告）日：1997-07-01

  Compounds of formula I ##STR1## or their hydroxy-protected derivatives, and compounds of formula I' ##STR2## wherein T is an acyl radical of formula Z ##STR3## wherein R.sup.z is unsubstituted or substituted hydrocarbyl wherein at least one carbon atom has been replaced by a hetero atom with the proviso that a hetero atom is not bonded directly to the carbonyl to which the radical R.sup.z is bonded, alkyl having two or more carbon atoms, lower alkenyl, lower alkynyl, aryl or unsubstituted or substituted amino, and wherein the radicals R.sub.1, B.sub.1, R.sub.2, R.sub.3, A.sub.1, A.sub.2 and NR.sub.4 R.sub.5 are as defined in the description, and precursors thereof, are described. The compounds have pharmaceutical activity, for example in the treatment of retroviral diseases, such as AIDS.

  公式I的化合物##STR1##或其羟基保护衍生物，以及公式I'的化合物##STR2##，其中T是公式Z的酰基自由基##STR3##，其中R.sup.z是不取代或取代的碳氢化合物，至少有一个碳原子被杂原子替换，但需满足杂原子不直接与R.sup.z连接的酰基相连，烷基含有两个或更多碳原子，低级烯基，低级炔基，芳基或不取代或取代的氨基，且其中R.sub.1、B.sub.1、R.sub.2、R.sub.3、A.sub.1、A.sub.2和NR.sub.4 R.sub.5如描述中定义，以及它们的先驱物，都有药物活性，例如在治疗反转录病毒疾病，如艾滋病。
• Synthesis, antiviral activity, and pharmacokinetic evaluation of P3 pyridylmethyl analogs of oximinoarylsulfonyl HIV-1 protease inhibitors
  作者：John T. Randolph、Peggy P. Huang、William J. Flosi、David DeGoey、Larry L. Klein、Clinton M. Yeung、Charles Flentge、Mingua Sun、Chen Zhao、Tatyana Dekhtyar、Hongmei Mo、Lynn Colletti、Warren Kati、Kennan C. Marsh、Akhteruzzaman Molla、Dale J. Kempf

  DOI：10.1016/j.bmc.2006.02.013

  日期：2006.6

  As a continuation of the recently communicated discovery of oximinoarylsulfonamides as potent inhibitors of HIV-1 aspartyl protease, compounds bearing pyridylmethyl substituents at P3 were designed and synthesized. Potent analogs in this series provided low single-digit nanomolar EC50 values against both wild-type HIV and resistant mutant virus (A17), attenuated some 3- to 12-fold in the presence of

  作为最近传达的氧亚氨基芳基磺酰胺作为HIV-1天冬氨酰蛋白酶的有效抑制剂的发现的继续，设计并合成了在P3带有吡啶基甲基取代基的化合物。该系列中的强效类似物对野生型HIV和抗性突变病毒（A17）均具有较低的个位数纳摩尔EC50值，在50％的人血清中可减弱约3至12倍。当与等量的利托那韦（每只5mg / kg）在大鼠中共同给药时，该系列化合物的药代动力学结果显示良好至极好的暴露，平均AUC> 8 microg h / mL。狗的相似剂量导致血浆水平显着降低（平均AUC <2 microg h / mL）。3-吡啶基甲基类似物30的总体暴露最佳（大鼠AUC = 7.1微克h / mL，狗AUC = 4.9微克h / mL），但是，
• [EN] NOVEL SULFONE AMIDE DERIVATIVES CAPABLE OF INHIBITING BACE<br/>[FR] NOUVEAUX DERIVES SULFONAMIDE CAPABLES D'INHIBER BACE
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2005030709A1

  公开（公告）日：2005-04-07

  The present invention relates to novel derivatives of sulfone amide of Formula 1 as defined in this disclosure which inhibit the activity of BACE (or beta-secretase). These sulfone amide derivatives are useful for the treatment and prevention of Alzheimer's disease and related diseases caused by production of beta-amyloid, by inhibiting the activity of BACE.

  本发明涉及本公开中定义的式1的磺酰脒衍生物，该衍生物抑制BACE（或β-分泌酶）的活性。这些磺酰脒衍生物可用于治疗和预防由β-淀粉样蛋白产生引起的阿尔茨海默病及相关疾病，通过抑制BACE的活性。
• 一种制备硫酸阿扎拉韦中间体的方法
  申请人：淮海工学院

  公开号：CN109942514B

  公开（公告）日：2022-09-09

  本发明公开了一种制备硫酸阿扎拉韦中间体(2R,3S)‑1,2‑环氧‑3‑叔丁氧羰基氨基‑4‑苯基丁烷的方法，该方法以廉价的L‑苯丙氨酸为起始原料，经与二碳酸二叔丁酯反应保护氨基、与醋酐缩合、与盐酸发生氯代后再在手性催化剂作用下发生不对称氢化还原，最后在碱性条件下环合即制得目标产物。本发明提供的硫酸阿扎拉韦重要中间体(2R,3S)‑1,2‑环氧‑3‑叔丁氧羰基氨基‑4‑苯基丁烷的制备方法原料廉价易得，反应条件温和，合成效率高，适于工业化生产，为制备硫酸阿扎拉韦及中间体提供了一条高效的途径。