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59768-74-0

59768-74-0

Identification

  • Product Name:L-Aspartic acid,N-[(1,1-dimethylethoxy)carbonyl]-, 4-methyl ester

  • CAS Number: 59768-74-0

  • EINECS:

  • Molecular Weight:247.248

  • Molecular Formula: C10H17NO6

  • HS Code:29241990

  • Mol File:59768-74-0.mol

Synonyms:(S)-2-(tert-Butoxycarbonylamino)-4-methoxy-4-oxobutanoicacid;Boc-L-aspartic acid b-methyl ester;N-tert-Butoxycarbonylaspartic acid b-methyl ester;Boc-Asp(OMe)-OH·DCHA;

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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

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  • Manufacture/Brand:TRC
  • Product Description:Boc-L-asparticAcidβ-MethylEster
  • Packaging:2g
  • Price:$ 70
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Boc-Asp(OMe)-OH ≥98.0% (TLC)
  • Packaging:5g
  • Price:$ 87.1
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:Boc-Asp(OMe)-OH 97%
  • Packaging:25g
  • Price:$ 104
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  • Manufacture/Brand:ChemScene
  • Product Description:Boc-Asp(OMe)-OH ≥98%
  • Packaging:100g
  • Price:$ 170
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:Boc-Asp(OMe)-OH ≥98%
  • Packaging:25g
  • Price:$ 50
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  • Manufacture/Brand:ChemScene
  • Product Description:Boc-Asp(OMe)-OH ≥98%
  • Packaging:500g
  • Price:$ 604
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  • Manufacture/Brand:chempep
  • Product Description:Boc-Asp(OMe)-OH >=98%
  • Packaging:100g
  • Price:$ 600
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  • Manufacture/Brand:chempep
  • Product Description:Boc-Asp(OMe)-OH >=98%
  • Packaging:25g
  • Price:$ 200
  • Delivery:In stock
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  • Manufacture/Brand:Chem-Impex
  • Product Description:Boc-L-asparticacidb-methylesterdicyclohexylammoniumsalt,≥98%(HPLC) ≥98%(HPLC)
  • Packaging:25G
  • Price:$ 64.06
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  • Manufacture/Brand:Chem-Impex
  • Product Description:Boc-L-asparticacidβ-methylester,99%(HPLC) 99%(HPLC)
  • Packaging:25G
  • Price:$ 61.6
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Relevant articles and documentsAll total 21 Articles be found

Stereoselective Synthesis of Protected l - Allo -Enduracididine and l -Enduracididine via Asymmetric Nitroaldol Reaction

Doi, Takayuki,Ganesan, A.,Masuda, Yuichi,Ohsawa, Kosuke,Thomas, Carys,Tokunaga, Takuya,Zhao, Hongbin

supporting information, p. 942 - 948 (2020/03/23)

The diastereoselecetive and scalable synthesis of cyclic guanidine-containing nonproteinoginic amino acids, enduracididines, has been achieved. Both diastereomers, l - allo -enduracididine and l -enduracididine, were prepared via catalyst-controlled asymmetric nitroaldol reaction with the aldehyde precursor derived from l -aspartic acid. The cyclic guanidine of di-Cbz-protected l - allo -enduracididine was fully protected with an allyl group to suppress nucleophilic side reactions. Introduced allyl group was efficiently removed via π-allylpalladium chemistry without attaching the Cbz group on the cyclic guanidine moiety.

COMPLEX

-

Paragraph 0070-0072, (2019/11/03)

PROBLEM TO BE SOLVED: To provide a substance that can be used in a simple quantitative method for desmosines. SOLUTION: In the complex of the present invention, desmosine is bound to a protein directly or via a linking group at the side chain terminal of the 4-position of the pyridine ring of desmosine. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Process for preparing deuterated desmosine and derivatives thereof

-

Page/Page column 6; 7; 10, (2019/05/18)

There is provided a process for preparing a compound represented by the following general formula (1) or a salt thereof, which comprises exchanging one or more of an amino proton in a compound represented by the following general formula (2) or a salt thereof to deuterium, and after the exchanging, converting a deuterium-exchanged compound of the compound represented by the general formula (2) or a salt thereof into the compound represented by the general formula (1) or a salt thereof: wherein, in the general formula (1), one, or two or more of hydrogen atom may be substituted with their isotope; and in the general formula (2), each of R1 is independently hydrogen atom, tert-butyloxycarbonyl group or benzyloxycarbonyl group, and R2 is independently tert-butyl group, benzyl group, methyl group or ethyl group.

Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives

Takaishi, Tomohiro,Wakisaka, Kyosuke,Vavricka, Christopher J.,Kiyota, Hiromasa,Izumi, Minoru

, p. 2126 - 2134 (2019/04/04)

Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.

Synthesis of desmosine-d4: Improvement of isotopic purity by D-H exchange of amino groups

Watanabe, Daisuke,Suzuki, Rina,Usuki, Toyonobu

supporting information, p. 1194 - 1197 (2017/03/02)

Desmosine is a crosslinking pyridinium amino acid of elastin, which is a useful biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD) by LC–MS/MS analysis. We previously reported a synthesis of desmosine-d4, which is useful as an internal standard for quantitative LC–MS/MS analysis of desmosines, by deuterogenation of an alkyne group; however, the isotopic purity of the desmosine-d4was only ca. 50%. The present report describes a new synthesis of desmosine-d4that improves the isotopic purity to ca. 90% by exchanging the protons of the amino groups to deuterium using deuterogenation.

Process route upstream and downstream products

Process route

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

di-tert-butyl dicarbonate

(+)-β-methyl-L-aspartate hydrochloride
16856-13-6

(+)-β-methyl-L-aspartate hydrochloride

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

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

Conditions
Conditions Yield
With sodium carbonate; In 1,4-dioxane; Ambient temperature;
95%
With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 18h;
91%
With sodium carbonate; In 1,4-dioxane; water; 1.) 0 deg C, 1 h, 2a.) 0 deg C, 1 h, 2b.) RT, 12 h;
81%
With sodium hydrogencarbonate; In methanol;
75%
(+)-β-methyl-L-aspartate hydrochloride; With sodium carbonate; In 1,4-dioxane; water; at 0 ℃; for 0.5h;
di-tert-butyl dicarbonate; In 1,4-dioxane; water; at 0 - 20 ℃;
75%
In tetrahydrofuran;
With sodium carbonate; In 1,4-dioxane; water; at 40 ℃; for 18h;
7.03 g
With sodium carbonate; In 1,4-dioxane; water; at 0 - 40 ℃; for 18h;
7.03 g
α-benzyl β-methyl N<sup>α</sup>-tert-butoxycarbonyl-(S)-aspartate
158201-15-1

α-benzyl β-methyl Nα-tert-butoxycarbonyl-(S)-aspartate

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

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

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 2h; under 2068.65 Torr;
100%
With hydrogen; palladium on activated charcoal; In ethyl acetate;
With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h;
1.36 g
β-methyl L-aspartate
2177-62-0

β-methyl L-aspartate

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

di-tert-butyl dicarbonate

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

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

Conditions
Conditions Yield
With sodium carbonate; Inert atmosphere;
75%
With sodium hydroxide; In 1,4-dioxane;
With sodium carbonate; In 1,4-dioxane; at 20 ℃; for 12h;
With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 25h;
24.8 g
With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 18h;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-2-amino-4-methoxy-4-oxobutanoic acid hydrochloride

(S)-2-amino-4-methoxy-4-oxobutanoic acid hydrochloride

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

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

Conditions
Conditions Yield
(S)-2-amino-4-methoxy-4-oxobutanoic acid hydrochloride; With sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 0.5h;
di-tert-butyl dicarbonate; In tetrahydrofuran; water; at 5 - 20 ℃;
2.54 g
(+)-β-methyl-L-aspartate hydrochloride
16856-13-6

(+)-β-methyl-L-aspartate hydrochloride

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

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

Conditions
Conditions Yield
With di-tert-butyl dicarbonate; sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;
89%
(3S,4S)-3-tert-Butoxycarbonylamino-4,5-dihydroxy-pentanoic acid methyl ester
1054666-03-3

(3S,4S)-3-tert-Butoxycarbonylamino-4,5-dihydroxy-pentanoic acid methyl ester

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

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

Conditions
Conditions Yield
With potassium permanganate; sodium periodate; sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 0.75h;
2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester
30925-18-9

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

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

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: DMAP; EDC-HCl / CH2Cl2 / 20 °C
2: H2 / Pd/C / ethyl acetate
With dmap; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In dichloromethane; ethyl acetate;
dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

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

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

Conditions
Conditions Yield
dimethyl N-tert-butoxycarbonyl-L-aspartate; With lithium hydroxide; In ethanol; water; at -10 ℃; pH=10;
With hydrogenchloride; In water; pH=3;
41.2 g
methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
784191-90-8

methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate

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

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: p-toluenesulfonic acid / methanol / 18 h / 20 °C
2: Na2CO3; NaIO4; KMnO4 / dioxane; H2O / 0.75 h / 20 °C
With potassium permanganate; sodium periodate; sodium carbonate; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; water;
[(R)-Benzenesulfonyl-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamic acid tert-butyl ester

[(R)-Benzenesulfonyl-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamic acid tert-butyl ester

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

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

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: Zn / tetrahydrofuran / 0.5 h / 20 °C
1.2: tetrahydrofuran / 1 h / 20 °C
2.1: p-toluenesulfonic acid / methanol / 18 h / 20 °C
3.1: Na2CO3; NaIO4; KMnO4 / dioxane; H2O / 0.75 h / 20 °C
With potassium permanganate; sodium periodate; sodium carbonate; toluene-4-sulfonic acid; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; water;

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