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Cas Database

136703-59-8

136703-59-8

Identification

Synonyms:methyl (3S)-3-(N-BOC-amino)-4-hydroxybutanoate;methyl 3-(S)-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate;methyl 3-(S)-(t-butoxycarbonylamino)-4-hydroxybutanoate;Butanoic acid, 3-[[(1,1-diMethylethoxy)carbonyl]aMino]-4-hydroxy-, Methyl ester, (3S)-;(S)-methyl [3-(tert-butoxycarbonyl)amino]-4-hydroxybutanoate;(S)-methyl 3-(t-butoxycarbonylamino)-4-hydroxybutanoate;methyl 3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:(3S)?-3-[[(1,1-Dimethylethoxy)?carbonyl]?amino]?-4-hydroxy-butanoicAcidMethylEster
  • Packaging:2.5g
  • Price:$ 1230
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:AK Scientific
  • Product Description:Methyl(S)-3-(Boc-amino)-4-hydroxybutanoate
  • Packaging:1g
  • Price:$ 505
  • Delivery:In stock
  • Buy Now

Relevant articles and documentsAll total 23 Articles be found

Click glycoconjugation of per-azido- and alkynyl-functionalized β-peptides built from aspartic acid

Barra, Marielle,Roy, Olivier,Traikia, Mounir,Taillefumier, Claude

, p. 2941 - 2955 (2010)

Azide- and alkynyl-containing homo-β3-peptides, of up to six residues in length, were synthesised in solution from aspartic acid. Their subsequent conjugation with monosaccharides bearing an azide or a terminal alkyne function was efficiently achieved by copper-mediated cycloadditions leading to two novel families of small glycoclusters. These compounds represent ideal tools to explore carbohydrate-mediated multivalent interactions.

Access to 2,6-Disubstituted 4-Oxopiperidines Using a 6-Endo-trig Cyclization: Stereoselective Synthesis of Spruce Alkaloid and (+)-241D

Harkiss, Alexander H.,Sutherland, Andrew

, p. 535 - 542 (2018)

A synthetic route to cis-2-methyl-4-oxo-6-alkylpiperidines has been developed using a 6-endo-trig cyclization of (E)-enones. The base-mediated intramolecular cyclization was found to be general for both alkyl- and aryl-substituted enones, providing the corresponding 4-oxopiperidines in high yields (80-89%). Stereoselective reduction of the 2,6-cis-disubstituted 4-oxopiperidines then gave the 2,4,6-cis,cis-trisubstituted 4-hydroxypiperidines in high diastereoselectivity. The general nature of this approach was demonstrated with the synthesis of the natural products, spruce alkaloid and (+)-241D.

Synthesis of a chiral β-amino acid derivative by a cobalt-catalysed coupling reaction

Pan, Xianhua,Yu, Wansheng,Ou, Wenhua,Tao, Xiaohu,Wan, Jiaomei,Liu, Feng

, p. 545 - 546 (2011)

A chiral β-amino acid derivative was synthesised by a cobalt-catalysed alkylation of 2,4,5-trifluorophenyl magnesium bromide with the alkyl halide derivative of L-aspartic acid, using an efficient catalytic reagent: CoCl 2/TMEDA. The halide der

5-MEMBERED HETEROARYL COMPOUNDS CONTAINING A HYDROXAMATE MOIETY AND THEIR USE

-

Page/Page column 76-78, (2020/07/31)

The present invention is directed to 5-membered heteroaryl compounds containing a hydroxamate moiety of Formula I, pharmaceutically acceptable salts or solvates thereof, and their use as sensitizers for chemotherapy of malignant tumors.

Method for producing pyrazole derivative

-

Paragraph 0252, (2018/08/30)

PROBLEM TO BE SOLVED: To provide a method for producing a pyrazole derivative. SOLUTION: There is provided the method for producing a pyrazole derivative by using a compound represented by formula (IIC), (IID) or (III) and a compound represented by formula (IV). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Stereoselective synthesis of 2,6-: Trans -4-oxopiperidines using an acid-mediated 6- endo-trig cyclisation

Bell, Jonathan D.,Harkiss, Alexander H.,Wellaway, Christopher R.,Sutherland, Andrew

, p. 6410 - 6422 (2018/10/02)

An acid-mediated 6-endo-trig cyclisation of amine-substituted enones has been developed for the stereoselective synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines. Performed under conditions that prevent removal of the Boc-protecting group or acetal formation, the key cyclisation was found to generate cleanly the 4-oxopiperidine products in high overall yields from a wide range of alkyl substituted enones. The synthetic utility of the trans-6-alkyl-2-methyl-4-oxopiperidines formed from this process was demonstrated with the total synthesis of the quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (-)-solenopsin A.

PYRAZOLE DERIVATIVE, OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

-

Paragraph 0235, (2018/05/16)

[Problem] The present invention is to provide a novel pyrazole derivative, or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the same, and a pharmaceutical use thereof. [Solution] The present invention provides a compound represented by the formula (I) or a pharmaceutically acceptable salt thereof, which has TRPM8 inhibitory effects: wherein ring A is C6-10 aryl or the like; X is CR4a or the like; R1 and R2 are a hydrogen atom or the like; R3 is a hydrogen atom or the like; R4 is a hydrogen atom or the like; ring B is C6-10 aryl or the like; R5 is a hydrogen atom or the like; R6a is a hydrogen atom or the like; R7a is a hydrogen atom or the like; R7b is a hydrogen atom or the like; R6b is a hydrogen atom or the like; R8 is a hydrogen atom or the like; n is 0, 1 or 2. Therefore, the compound represented by the formula (I) of the present invention or a pharmaceutically acceptable salt thereof is useful as an agent for treating or preventing diseases or symptoms caused by hyperexcitability or disorder of afferent neurons.

Process route upstream and downstream products

Process route

(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester
59768-74-0,124184-67-4

(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In ethyl acetate; at 0 - 20 ℃; for 16h; Inert atmosphere;
With sodium tetrahydroborate; In tetrahydrofuran; water; for 0.1h; Inert atmosphere;
90%
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 0 ℃;
79%
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester; With 4-methyl-morpholine; chloroformic acid ethyl ester; In tetrahydrofuran; at -10 ℃; for 0.166667h;
With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h; Further stages.;
76%
With diborane; In tetrahydrofuran; at 0 ℃;
76%
With sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; Multistep reaction; 1.) CH2Cl2, r.t., 3 h; 2.) THF, EtOH, 0 deg C, 15 min;
Multi-step reaction with 2 steps
1: DCC / CH2Cl2 / 12 h / 20 °C
2: NaBH4 / tetrahydrofuran; ethanol / 0.25 h / 0 °C
With sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane;
Multi-step reaction with 2 steps
1: 100 percent / DCC / ethyl acetate / 20 °C
2: 83 percent / aq. NaBH4 / tetrahydrofuran / 0.04 h / 0 °C
With sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate; 1: Esterification / 2: Reduction;
Multi-step reaction with 2 steps
1: DCC
2: aq. NaBH4 / tetrahydrofuran
With sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran;
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester; With 4-methyl-morpholine; chloroformic acid ethyl ester; In tetrahydrofuran; at -10 ℃; for 0.25h;
In tetrahydrofuran; methanol; at -15 - -10 ℃; for 0.833333h;
With hydrogenchloride; In water; pH=2;
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide / ethyl acetate / 0 - 20 °C
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.5 h / 0 °C
With sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethyl acetate;
With 4-methyl-morpholine; chloroformic acid ethyl ester; In tetrahydrofuran; for 1h; Cooling with ice;
10.82 g
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide / dichloromethane; ethyl acetate / 20 h / 0 - 20 °C
2: sodium tetrahydroborate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere
With sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate;
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at 0 ℃; for 1h;
With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;
1.18 g
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide / ethyl acetate / 16 h / 0 - 20 °C / Inert atmosphere
2: sodium tetrahydroborate / tetrahydrofuran; water / 0.1 h / 20 °C / Inert atmosphere
With sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; ethyl acetate;
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide / ethyl acetate / 16 h / 0 - 20 °C
2: sodium tetrahydroborate / tetrahydrofuran; water / 0.25 h / 0 °C
With sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; ethyl acetate;
Boc-L-Asp(β-methyl)-N-hydroxysuccinimide
139519-25-8

Boc-L-Asp(β-methyl)-N-hydroxysuccinimide

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 0.0416667h;
83%
With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 0 ℃; for 0.25h;
With sodium tetrahydroborate; In tetrahydrofuran; water; Inert atmosphere;
With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 0.5h;
19.6 g
With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere;
0.7 g
With sodium tetrahydroborate; In tetrahydrofuran; water; at 20 ℃; for 0.1h; chemoselective reaction; Inert atmosphere;
7.03 g
With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 ℃; for 0.25h;
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester
59768-74-0,124184-67-4

(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester

isobutyl chloroformate
543-27-1

isobutyl chloroformate

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester; isobutyl chloroformate; With 4-methyl-morpholine; In tetrahydrofuran; at 0 ℃; for 1h;
With methanol; sodium tetrahydroborate; at 0 ℃; for 1h;
1.18 g
dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
With sodium tetrahydroborate; In methanol; at -10 ℃;
75%
(S)-3-tert-Butoxycarbonylamino-4-(2,5-dioxo-pyrrolidin-1-yl)-4-oxo-butyric acid methyl ester

(S)-3-tert-Butoxycarbonylamino-4-(2,5-dioxo-pyrrolidin-1-yl)-4-oxo-butyric acid methyl ester

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
With sodium tetrahydroborate; In tetrahydrofuran;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 95 percent / 0.5M aq.Na2CO3 / dioxane / Ambient temperature
2: 1.) N-hydroxysuccinimide, DCC; 2.) NaBH4 / 1.) CH2Cl2, r.t., 3 h; 2.) THF, EtOH, 0 deg C, 15 min
With sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; sodium carbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane;
Multi-step reaction with 5 steps
1: triethylamine / 1,4-dioxane; water / 0 - 20 °C
2: triethylamine / tetrahydrofuran / 0 °C
3: sodium tetrahydroborate / water / 1 h / 20 °C
4: palladium 10% on activated carbon; hydrogen / 20 °C
5: tetrahydrofuran; methanol / 1 h / 0 °C
With sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; water;
Multi-step reaction with 2 steps
1: sodium hydroxide / tert-butyl alcohol; water
2: potassium carbonate / N,N-dimethyl-formamide
With potassium carbonate; sodium hydroxide; In water; N,N-dimethyl-formamide; tert-butyl alcohol;
(S)-methyl 4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)butanoate

(S)-methyl 4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)butanoate

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
methanol
67-56-1

methanol

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-aspartic acid hydrochloride
17585-59-0

L-aspartic acid hydrochloride

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
methanol; L-aspartic acid hydrochloride; With thionyl chloride; at -10 ℃;
di-tert-butyl dicarbonate; With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 12h; Further stages;
β-methyl L-aspartate
2177-62-0

β-methyl L-aspartate

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: aq. Na2CO3 / dioxane / 12 h / 20 °C
2: DCC / CH2Cl2 / 12 h / 20 °C
3: NaBH4 / tetrahydrofuran; ethanol / 0.25 h / 0 °C
With sodium tetrahydroborate; sodium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane;
BOC-L-aspartic acid 4-benzyl ester
7536-58-5,98482-77-0

BOC-L-aspartic acid 4-benzyl ester

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester
136703-59-8

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: triethylamine / tetrahydrofuran / 0 °C
2: sodium tetrahydroborate / water / 1 h / 20 °C
3: palladium 10% on activated carbon; hydrogen / 20 °C
4: tetrahydrofuran; methanol / 1 h / 0 °C
With sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; triethylamine; In tetrahydrofuran; methanol; water;

Global suppliers and manufacturers

Global( 2) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Kono Chem Co.,Ltd
  • Business Type:Other
  • Contact Tel:86-29-86107037-8015
  • Emails:info@konochemical.com
  • Main Products:82
  • Country:China (Mainland)
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