Welcome to LookChem.com Sign In|Join Free

Cas Database

349148-42-1

349148-42-1

Identification

Synonyms:(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

Safety information and MSDS

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase

Relevant articles and documentsAll total 1 Articles be found

Synthesis of optically active 2-alkyl-3,4-iminobutanoic acids. β-amino acids containing an aziridine heterocycle

Park,Tian,Kim

, p. 3696 - 3703 (2007/10/03)

All four stereoisomers of 2-alkyl-3,4-iminobutanic acid, a novel class of β-amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the β-position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the α-carboxylate and α-amino groups. The α-carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.

Process route upstream and downstream products

Process route

(2R,3S)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester
349148-38-5

(2R,3S)-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid methyl ester

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Conditions
Conditions Yield
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 3h;
82%
benzyl bromide
100-39-0

benzyl bromide

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
1.2: 56 percent / tetrahydrofuran; hexane / 6 h
2.1: acetyl chloride / methanol / 3 h / 0 °C
2.2: CuCO3*Cu(OH)2 / H2O / 3 h / 70 °C
3.1: 5.8 g / Na2CO3 / H2O / 4 h / 20 °C
4.1: DCC / 1,2-dimethoxy-ethane
5.1: 7.3 g / NaBH4 / tetrahydrofuran / 18 h / 0 - 20 °C
6.1: 82 percent / DEAD; PPh3 / tetrahydrofuran / 3 h / 0 °C
With sodium tetrahydroborate; sodium carbonate; acetyl chloride; dicyclohexyl-carbodiimide; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; water; 6.1: Intramolecular Mitsunobu reaction;
dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
1.2: 56 percent / tetrahydrofuran; hexane / 6 h
2.1: acetyl chloride / methanol / 3 h / 0 °C
2.2: CuCO3*Cu(OH)2 / H2O / 3 h / 70 °C
3.1: 5.8 g / Na2CO3 / H2O / 4 h / 20 °C
4.1: DCC / 1,2-dimethoxy-ethane
5.1: 7.3 g / NaBH4 / tetrahydrofuran / 18 h / 0 - 20 °C
6.1: 82 percent / DEAD; PPh3 / tetrahydrofuran / 3 h / 0 °C
With sodium tetrahydroborate; sodium carbonate; acetyl chloride; dicyclohexyl-carbodiimide; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; water; 6.1: Intramolecular Mitsunobu reaction;
(2S,3R)-N-tert-butyloxycarbonyl-3-benzylaspartic acid dimethyl ester
349464-80-8

(2S,3R)-N-tert-butyloxycarbonyl-3-benzylaspartic acid dimethyl ester

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: acetyl chloride / methanol / 3 h / 0 °C
1.2: CuCO3*Cu(OH)2 / H2O / 3 h / 70 °C
2.1: 5.8 g / Na2CO3 / H2O / 4 h / 20 °C
3.1: DCC / 1,2-dimethoxy-ethane
4.1: 7.3 g / NaBH4 / tetrahydrofuran / 18 h / 0 - 20 °C
5.1: 82 percent / DEAD; PPh3 / tetrahydrofuran / 3 h / 0 °C
With sodium tetrahydroborate; sodium carbonate; acetyl chloride; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; 5.1: Intramolecular Mitsunobu reaction;
(2S,3R)-N-benzyloxycarbonyl-3-benzylaspartic acid 4-methyl ester
349148-33-0

(2S,3R)-N-benzyloxycarbonyl-3-benzylaspartic acid 4-methyl ester

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: DCC / 1,2-dimethoxy-ethane
2: 7.3 g / NaBH4 / tetrahydrofuran / 18 h / 0 - 20 °C
3: 82 percent / DEAD; PPh3 / tetrahydrofuran / 3 h / 0 °C
With sodium tetrahydroborate; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; 3: Intramolecular Mitsunobu reaction;
(2R,3S)-2-Amino-3-benzyl-succinic acid 4-methyl ester; hydrochloride

(2R,3S)-2-Amino-3-benzyl-succinic acid 4-methyl ester; hydrochloride

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 5.8 g / Na2CO3 / H2O / 4 h / 20 °C
2: DCC / 1,2-dimethoxy-ethane
3: 7.3 g / NaBH4 / tetrahydrofuran / 18 h / 0 - 20 °C
4: 82 percent / DEAD; PPh3 / tetrahydrofuran / 3 h / 0 °C
With sodium tetrahydroborate; sodium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; water; 4: Intramolecular Mitsunobu reaction;
(2S,3R)-2-Benzyl-3-benzyloxycarbonylamino-succinic acid 4-(2,5-dioxo-pyrrolidin-1-yl) ester 1-methyl ester

(2S,3R)-2-Benzyl-3-benzyloxycarbonylamino-succinic acid 4-(2,5-dioxo-pyrrolidin-1-yl) ester 1-methyl ester

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 7.3 g / NaBH4 / tetrahydrofuran / 18 h / 0 - 20 °C
2: 82 percent / DEAD; PPh3 / tetrahydrofuran / 3 h / 0 °C
With sodium tetrahydroborate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 2: Intramolecular Mitsunobu reaction;
(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

(2R,3S)-2-benzyl-3,4-iminobutanoic acid methyl ester
349148-46-5

(2R,3S)-2-benzyl-3,4-iminobutanoic acid methyl ester

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In methanol; for 2h;
95%
(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester
349148-42-1

(2R,3S)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

Lithium; (R)-2-(S)-aziridin-2-yl-3-phenyl-propionate

Lithium; (R)-2-(S)-aziridin-2-yl-3-phenyl-propionate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 95 percent / H2 / Pd/C / methanol / 2 h
2: 85 percent / LiOH / methanol; H2O / 4 h / 0 °C
With lithium hydroxide; hydrogen; palladium on activated charcoal; In methanol; water;

Global suppliers and manufacturers

Global( 0) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 349148-42-1
Post Buying Request Now
close
Remarks: The blank with*must be completed