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Cas Database

34290-72-7

34290-72-7

Identification

  • Product Name:Glycine, 1-[(1,1-dimethylethoxy)carbonyl]-L-prolyl-, methyl ester

  • CAS Number: 34290-72-7

  • EINECS:

  • Molecular Weight:286.328

  • Molecular Formula: C13H22N2O5

  • HS Code:

  • Mol File:34290-72-7.mol

Synonyms:N-tert-butoxycarbonyl-L-prolyl-glycine methyl ester;Boc-Pro-Gly-OMe;tert-butyloxycarbonyl-prolyl-glycine methyl ester;

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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:SynQuest Laboratories
  • Product Description:N-Boc-Pro-Gly-OMe
  • Packaging:5 g
  • Price:$ 1064
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-Boc-Pro-Gly-OMe
  • Packaging:1 g
  • Price:$ 280
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  • Manufacture/Brand:Crysdot
  • Product Description:(S)-tert-Butyl2-((2-methoxy-2-oxoethyl)carbamoyl)pyrrolidine-1-carboxylate 95+%
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  • Price:$ 447
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  • Manufacture/Brand:Chemenu
  • Product Description:(S)-tert-Butyl2-((2-methoxy-2-oxoethyl)carbamoyl)pyrrolidine-1-carboxylate 95%
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  • Manufacture/Brand:Alichem
  • Product Description:(S)-tert-Butyl2-((2-methoxy-2-oxoethyl)carbamoyl)pyrrolidine-1-carboxylate
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  • Manufacture/Brand:AK Scientific
  • Product Description:N-Boc-Pro-Gly-OMe
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  • Manufacture/Brand:Activate Scientific
  • Product Description:N-Boc-Pro-Gly-OMe 97%
  • Packaging:5 g
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  • Manufacture/Brand:Activate Scientific
  • Product Description:N-Boc-Pro-Gly-OMe 97%
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Relevant articles and documentsAll total 23 Articles be found

N-Terminal Selective C?H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification

Allouche, Emmanuelle M. D.,Simonet-Davin, Rapha?l,Waser, Jerome

supporting information, (2022/02/25)

A methodology for the C?H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at the carbamate-protected N-terminal residue in presence of the numerous other functional groups present on the molecules. Post-functionalizations of the obtained aminal compounds were achieved: cycloaddition reactions or C?C bond formations via a sequence of imine formation/nucleophilic addition were performed, offering an easy access to diversified peptides.

Highly Diastereoselective Synthesis of Cyclic α-Aminophosphonic and α-Aminophosphinic Acids from Glycyl-l-Proline 2,5-Diketopiperazine

Ordó?ez, Mario,Torres-Hernández, Fernando,Viveros-Ceballos, José Luis

, p. 7378 - 7383 (2019/11/26)

This paper describes the first diastereoselective synthesis of cyclic α-aminophosphonic and α-amino phosphonic acids from glycyl-l-proline 2,5-diketopiperazine (S)-6 prepared according to the usual peptide coupling procedures. The highlights of this contribution is the chemoselective reduction of the carbamate-imide activated carbonyl group in the N-Boc 2,5-diketopiperazine (S)-11 to generate the unstable hemiaminals (1R,8aS)-12 and (1S,8aS)-13, followed by the highly diastereoselective nucleophilic addition of trimethyl phosphite or dimethyl phenylphosphonite to the chiral carbenium ion (S)-5. Acid hydrolysis of the phosphonate and phosphinate functionalities with simultaneous cleavage of the tert-butyl carbamate protecting group led to the target compounds. The high diastereoselectivity in the nucleophilic addition of trivalent phosphorus to the chiral carbenium ion (S)-5 is in agreement with our precedent reports.

A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

Slobodyanyuk, Evgeniy Y.,Artamonov, Oleksiy S.,Kulik, Irene B.,Rusanov, Eduard,Volochnyuk, Dmitriy M.,Grygorenko, Oleksandr O.

, p. 11 - 17 (2018/02/06)

A convenient four-step approach to the synthesis of (S)-4-alkyl-2-(pyrrolidin-2-yl)oxazoles starting from l-Boc-proline inspired by naturally occurring oxazole-containing peptidomimetics is described. The key step is the cyclization of 1-Boc-N-(1-oxoalkan

Total Synthesis of the Cyclic Dodecapeptides Wewakazole and Wewakazole B

Inman, Martyn,Dexter, Hannah L.,Moody, Christopher J.

supporting information, p. 3454 - 3457 (2017/07/15)

The cyclic dodecapeptides wewakazole and wewakazole B have been synthesized by a divergent strategy via a common tris-proline containing oxazole octapeptide and two separate bis-oxazole containing tetrapeptide units, followed by peptide coupling and macro

Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents

Kumar, Vikas,Krishna, K. Vijaya,Khanna, Shruti,Joshi, Khashti Ballabh

, p. 5369 - 5376 (2016/08/05)

This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe–Gly and Pro–Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through va

Process route upstream and downstream products

Process route

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

glycine ethyl ester hydrochloride
5680-79-5,883886-67-7

glycine ethyl ester hydrochloride

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
With 4-methyl-morpholine; isobutyl chloroformate; In dichloromethane; at 20 ℃;
93%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 16h;
90%
1-(tert-butoxycarbonyl)-L-proline; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
glycine ethyl ester hydrochloride; With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere;
78%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;
73%
glycine ethyl ester hydrochloride; With 4-methyl-morpholine; In chloroform; at 0 ℃; for 0.25h;
1-(tert-butoxycarbonyl)-L-proline; With dicyclohexyl-carbodiimide; In chloroform; for 24h; Further stages.;
69.9%
With triethylamine; dicyclohexyl-carbodiimide; In chloroform; at 0 - 20 ℃;
68%
1-(tert-butoxycarbonyl)-L-proline; glycine ethyl ester hydrochloride; With dmap; triethylamine; In tetrahydrofuran; for 0.5h; Inert atmosphere;
With 3,5,5-trichloro-5H-dibenzo[b,d]silole; In tetrahydrofuran; at 20 - 60 ℃; Inert atmosphere;
66%
1-(tert-butoxycarbonyl)-L-proline; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); dichloromethane; at 0 ℃; for 0.5h;
glycine ethyl ester hydrochloride; With N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); dichloromethane; at 0 - 20 ℃; for 16h;
glycine ethyl ester hydrochloride; With triethylamine; In chloroform; at 0 ℃; for 0.25h;
1-(tert-butoxycarbonyl)-L-proline; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In chloroform; at 20 ℃; for 0.5h;
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 23 ℃; for 3h;
1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

methoxycarbonylmethylamine
616-34-2

methoxycarbonylmethylamine

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; cooling;
90%
With 4-methyl-morpholine; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; at -15 ℃; for 0.5h;
90%
79%
With dicyclohexyl-carbodiimide; In chloroform;
68%
Multistep reaction; activated-ester and mixed anhydride methods;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 40h;
1-(tert-butoxycarbonyl)-L-proline; With N-ethyl-N,N-diisopropylamine; isobutyl chloroformate;
methoxycarbonylmethylamine; With N-ethyl-N,N-diisopropylamine;
glycine ethyl ester hydrochloride
5680-79-5,883886-67-7

glycine ethyl ester hydrochloride

N-tert-butoxycarbonyl-proline
15761-39-4,59433-50-0

N-tert-butoxycarbonyl-proline

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
N-tert-butoxycarbonyl-proline; With 1-hydroxybenzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); dichloromethane; at 0 ℃; for 0.5h;
glycine ethyl ester hydrochloride; With N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); dichloromethane; at 0 - 20 ℃; for 26h;
N-tert-butyloxycarbonyl-L-prolylglycine
51785-82-1,250290-80-3

N-tert-butyloxycarbonyl-L-prolylglycine

methyl iodide
74-88-4

methyl iodide

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;
73%
1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: N,N-diisopropylethylamine; [bis(2-methoxyethyl)amino]sulfur trifluoride / CH2Cl2 / 0 °C
2: CH2Cl2 / 6.25 h / 0 - 20 °C
With N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane;
1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

methyl 2-aminoacetate TFA salt

methyl 2-aminoacetate TFA salt

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;
tert-butyl 2-(fluorocarbonyl)pyrrolidine-1-carboxylate
133010-05-6

tert-butyl 2-(fluorocarbonyl)pyrrolidine-1-carboxylate

methoxycarbonylmethylamine
616-34-2

methoxycarbonylmethylamine

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
In dichloromethane; at 0 - 20 ℃; for 6.25h;
1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0.08 h / Cooling with ice
2: dichloromethane / 5 h
With triethylamine; In dichloromethane;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / water / 20 °C
2: isobutyl chloroformate; 4-methyl-morpholine / dichloromethane / 20 °C
With 4-methyl-morpholine; sodium hydrogencarbonate; isobutyl chloroformate; In dichloromethane; water;
tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: triethylamine / methanol / 20 - 65 °C
2.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 1 h / 0 °C / Inert atmosphere
2.2: 12 h / 20 °C / Inert atmosphere
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

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