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Cas Database

63039-46-3

63039-46-3

Identification

Synonyms:Boc-D-Propargylglycine;N-tert-Butoxycarbonyl-D-Propargyl Glycine;(R)-N-tert-Butoxycarbonyl-2-amino-4-pentynoic acid;(2R)-2-(tert-butoxycarbonylamino)pent-4-ynoate;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin H332 Harmful if inhaled

  • 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 view more

  • Manufacture/Brand
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  • Manufacture/Brand:TRC
  • Product Description:Boc-D-Pra-OH
  • Packaging:500mg
  • Price:$ 75
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:D-2-Propargylglycine, N-Boc protected
  • Packaging:25 g
  • Price:$ 1312
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:D-2-Propargylglycine, N-Boc protected
  • Packaging:5 g
  • Price:$ 384
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:D-2-Propargylglycine, N-Boc protected
  • Packaging:1 g
  • Price:$ 160
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  • Manufacture/Brand:Oakwood
  • Product Description:N-Boc-2-Propargyl-D-glycine
  • Packaging:250mg
  • Price:$ 150
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  • Manufacture/Brand:Crysdot
  • Product Description:(R)-2-((tert-Butoxycarbonyl)amino)pent-4-ynoicacid 97%
  • Packaging:10g
  • Price:$ 282
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  • Manufacture/Brand:Crysdot
  • Product Description:(R)-2-((tert-Butoxycarbonyl)amino)pent-4-ynoicacid 97%
  • Packaging:25g
  • Price:$ 593
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  • Manufacture/Brand:ChemPep
  • Product Description:Boc-D-Gly(Propargyl)-OH
  • Packaging:25g
  • Price:$ 1350
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  • Manufacture/Brand:ChemPep
  • Product Description:Boc-D-Gly(Propargyl)-OH
  • Packaging:5g
  • Price:$ 450
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  • Manufacture/Brand:Chemenu
  • Product Description:(R)-2-((tert-Butoxycarbonyl)amino)pent-4-ynoicacid 97%
  • Packaging:10g
  • Price:$ 267
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Relevant articles and documentsAll total 5 Articles be found

D-ALA-D-ALA-BASED DIPEPTIDES AS TOOLS FOR IMAGING PEPTIDOGLYCAN BIOSYNTHESIS

-

Paragraph 0186-0190, (2016/08/29)

Disclosed herein are compositions for assessing peptidoglycan biosynthesis in bacteria using modified dipeptides containing a bioorthogonal tag and applying novel post-labeling methods to label the bioorthogonal tag. The resultant, labeled peptidoglycan structures are amenable for identifying bacteria by microscopic visualization.

N6-(2-(R)-propargylglycyl)lysine as a clickable pyrrolysine mimic

Li, Xin,Fekner, Tomasz,Chan, Michael K.

supporting information; experimental part, p. 1765 - 1769 (2011/03/22)

Clickable copycat! Readily available dipeptide d-Pra-ε-Lys is identified using a modified fluorescence protein assay as a highly efficient clickable pyrrolysine mimic. It is shown to incorporate into calmodulin in high yield to provide a handle for labeling with anazide-containing coumarin.

Synthesis, properties and crystal structure of the tripeptide boc-L-prolyl-L-propargylglycyl-glycine methylester

Willisch, Hans,Hiller, Wolfgang,Hemmasi, Bahram,Bayer, Ernst

, p. 3947 - 3958 (2007/10/02)

Propargylglycine, as a powerful inhibitor of microbial growth, was built into a protected tripeptide with the sequence Pro-Pra-Gly. The peptide was employed to study its effects on the activity of prolyl 4-hydroxylase and the collagen biosynthesis. The Boc-protected tripeptide methylester was identified by mass spectrometry and NMR spectroscopy and its crystal structure was established by X-ray diffraction analysis.

Process route upstream and downstream products

Process route

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

di-tert-butyl dicarbonate

(R)-2-aminopent-4-ynoic acid
23235-01-0,23235-03-2,50428-03-0,64165-64-6

(R)-2-aminopent-4-ynoic acid

(R)-2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid
61172-66-5,63039-48-5,143979-37-7,63039-46-3

(R)-2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid

Conditions
Conditions Yield
di-tert-butyl dicarbonate; (R)-2-aminopent-4-ynoic acid; With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; at 20 ℃; for 3h; Inert atmosphere;
With hydrogenchloride; In 1,4-dioxane; water; pH=1.5; Inert atmosphere;
97%
With sodium hydrogencarbonate; In 1,4-dioxane; water; for 4h; Heating;
83%
With potassium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;
With sodium carbonate; In water; acetonitrile; at 20 ℃; for 14.25h; Cooling with ice;
Conditions
Conditions Yield
(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid
61172-66-5,63039-46-3,63039-48-5,143979-37-7

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid

tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl]carbamate
1172623-98-1

tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl]carbamate

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: dichloromethane / 0.5 h / 20 °C
1.2: 3 h / 20 °C
2.1: isopropylmagnesium chloride / dichloromethane; tetrahydrofuran / 3 h / -20 °C
2.2: 13 h / 0 - 20 °C
3.1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-[(1R,2R)-1,2-diamino-2-(2-sulfonatophenyl)ethyl]benzene-1-sulfonate sodium; sodium formate; sodium dodecyl-sulfate / water; ethanol / 11 h / 20 - 40 °C
4.1: 1-hydroxy-pyrrolidine-2,5-dione; tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); triphenylphosphine / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere
With 1-hydroxy-pyrrolidine-2,5-dione; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-[(1R,2R)-1,2-diamino-2-(2-sulfonatophenyl)ethyl]benzene-1-sulfonate sodium; isopropylmagnesium chloride; sodium formate; sodium dodecyl-sulfate; tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid
61172-66-5,63039-46-3,63039-48-5,143979-37-7

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid

N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
951127-25-6

N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: chloroformic acid ethyl ester; 4-methyl-morpholine / 0.5 h / -10 °C
1.2: -10 °C
2.1: isopropylmagnesium chloride / tetrahydrofuran / 4 h / Large scale
3.1: aluminum isopropoxide; isopropyl alcohol / dichloromethane / 12 h / 40 °C
4.1: potassium hydroxide / methanol / 0 °C
4.2: 0 - 20 °C
5.1: sodium hydrogensulfate monohydrate; water / tetrahydrofuran / 30 - 35 °C
6.1: sodium carbonate / tetrahydrofuran / 65 °C
With 4-methyl-morpholine; sodium hydrogensulfate monohydrate; water; isopropylmagnesium chloride; chloroformic acid ethyl ester; aluminum isopropoxide; sodium carbonate; isopropyl alcohol; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 3.1: |Meerwein-Ponndorf-Verley Reduction;
Multi-step reaction with 6 steps
1.1: dichloromethane / 0.5 h / 20 °C
1.2: 3 h / 20 °C
2.1: isopropylmagnesium chloride / dichloromethane; tetrahydrofuran / 3 h / -20 °C
2.2: 13 h / 0 - 20 °C
3.1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-[(1R,2R)-1,2-diamino-2-(2-sulfonatophenyl)ethyl]benzene-1-sulfonate sodium; sodium formate; sodium dodecyl-sulfate / water; ethanol / 11 h / 20 - 40 °C
4.1: 1-hydroxy-pyrrolidine-2,5-dione; tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); triphenylphosphine / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere
5.1: tert-butyl methyl ether / 3 h / -10 °C
5.2: 3 h / 0 - 10 °C
5.3: 10 h / 20 °C
6.1: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / 1 h / -70 - 20 °C
With 1-hydroxy-pyrrolidine-2,5-dione; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); oxalyl dichloride; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-[(1R,2R)-1,2-diamino-2-(2-sulfonatophenyl)ethyl]benzene-1-sulfonate sodium; isopropylmagnesium chloride; sodium formate; sodium dodecyl-sulfate; tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; tert-butyl methyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
benzyl chloride
100-44-7

benzyl chloride

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid
61172-66-5,63039-46-3,63039-48-5,143979-37-7

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid

(S)-2-((tert-butoxycarbonyl)amino)-4-pentynoic acid benzyl ester
936242-42-1

(S)-2-((tert-butoxycarbonyl)amino)-4-pentynoic acid benzyl ester

Conditions
Conditions Yield
With N-ethyl-N,N-diisopropylamine; dmap; In dichloromethane; at 0 ℃; for 4h;
91%
benzyl chloroformate
501-53-1,94274-21-2

benzyl chloroformate

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid
61172-66-5,63039-46-3,63039-48-5,143979-37-7

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid

(S)-2-((tert-butoxycarbonyl)amino)-4-pentynoic acid benzyl ester
936242-42-1

(S)-2-((tert-butoxycarbonyl)amino)-4-pentynoic acid benzyl ester

Conditions
Conditions Yield
With N-ethyl-N,N-diisopropylamine; dmap; In dichloromethane; at 0 ℃; for 4h;
91%
With N-ethyl-N,N-diisopropylamine; dmap; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
91%
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
78%
(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid
61172-66-5,63039-46-3,63039-48-5,143979-37-7

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid

benzyl azide
622-79-7

benzyl azide

3-(1-benzyl-1<i>H</i>-[1,2,3]triazol-4-yl)-2-<i>tert</i>-butoxycarbonylamino-propionic acid
928838-27-1

3-(1-benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid

Conditions
Conditions Yield
With sodium L-ascorbate; copper diacetate; In water; tert-butyl alcohol; at 20 ℃;
62%
With sodium L-ascorbate; copper acetylacetonate; In water; tert-butyl alcohol; at 20 ℃;
62%
C<sub>19</sub>H<sub>20</sub>N<sub>2</sub>O<sub>2</sub>

C19H20N2O2

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid
61172-66-5,63039-46-3,63039-48-5,143979-37-7

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid

(S)-methyl 3-((N-benzyl-2-((tert-butoxycarbonyl)amino)pent-4-ynamido)methyl)-1-methyl-1H-indole-5-carboxylate

(S)-methyl 3-((N-benzyl-2-((tert-butoxycarbonyl)amino)pent-4-ynamido)methyl)-1-methyl-1H-indole-5-carboxylate

Conditions
Conditions Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;
80%
(S)-N-([1,1′-biphenyl]-4-ylmethyl)-2-amino-3-(1H-indol-3-yl)propanamide

(S)-N-([1,1′-biphenyl]-4-ylmethyl)-2-amino-3-(1H-indol-3-yl)propanamide

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid
61172-66-5,63039-46-3,63039-48-5,143979-37-7

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid

tert-butyl ((S)-1-(((S)-1-(([1,1′-biphenyl]-4-ylmethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-1-oxopent-4-yn-2-yl)carbamate

tert-butyl ((S)-1-(((S)-1-(([1,1′-biphenyl]-4-ylmethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-1-oxopent-4-yn-2-yl)carbamate

Conditions
Conditions Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;
82%
C<sub>45</sub>H<sub>62</sub>N<sub>8</sub>O<sub>9</sub>

C45H62N8O9

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid
61172-66-5,63039-46-3,63039-48-5,143979-37-7

(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid

C<sub>50</sub>H<sub>67</sub>N<sub>9</sub>O<sub>10</sub>

C50H67N9O10

Conditions
Conditions Yield
C45H62N8O9; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;
(S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere;
97%

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