Benzyl (S)-3-(Boc-amino)-4-iodobutanoate

Base Information

• Chemical Name: Benzyl (S)-3-(Boc-amino)-4-iodobutanoate
• CAS No.: 161529-22-2
• Molecular Formula: C16H22INO4
• Molecular Weight: 419.259
• Hs Code.: 2924297099
• DSSTox Substance ID: DTXSID001148180
• Mol file: 161529-22-2.mol

Synonyms:Benzyl (S)-3-(Boc-amino)-4-iodobutanoate;161529-22-2;Benzyl (3S)-4-iodo-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;SCHEMBL5218342;AZOOJSICMDXGFD-ZDUSSCGKSA-N;DTXSID001148180;AC4601;AKOS027256894;Benzyl(S)-3-(Boc-amino)-4-iodobutanoate;CS-0447598;Benzyl (S)-3-((tert-butoxycarbonyl)amino)-4-iodobutanoate;(S)-3-tert-butoxycarbonylamino-4-iodo-butyric acid benzyl ester;Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-iodobutanoate

Chemical Property of Benzyl (S)-3-(Boc-amino)-4-iodobutanoate

Chemical Property:

• Boiling Point: 476.6±40.0 °C(Predicted)
• PSA: 64.63000
• Density: 1.449±0.06 g/cm3(Predicted)
• LogP: 3.83910
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 419.05936
• Heavy Atom Count: 22
• Complexity: 362

Purity/Quality:

97% ^*data from raw suppliers

Benzyl (S)-3-(Boc-amino)-4-iodobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)OCC1=CC=CC=C1)CI
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC(=O)OCC1=CC=CC=C1)CI

Technology Process of Benzyl (S)-3-(Boc-amino)-4-iodobutanoate

There total 6 articles about Benzyl (S)-3-(Boc-amino)-4-iodobutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate (79069-16-2) → benzyl (S)-2-(N-t-butoxycarbonylamino)-4-iodobutanoate (161529-22-2)

Guidance literature:

With 1H-imidazole; polystyryl diphenyl phosphine-iodine; In dichloromethane; for 1h; Heating;

DOI:10.1016/0040-4039(94)02202-M

Reference yield:

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → benzyl (S)-2-(N-t-butoxycarbonylamino)-4-iodobutanoate (161529-22-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-methyl-morpholine / tetrahydrofuran / 0.25 h / 0 °C

2: sodium tetrahydroborate / water; tetrahydrofuran / 0 - 20 °C

3: triphenylphosphine; iodine; 1H-imidazole / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

With 4-methyl-morpholine; 1H-imidazole; sodium tetrahydroborate; iodine; triphenylphosphine; In tetrahydrofuran; water;

DOI:10.1007/s00726-012-1352-5

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → benzyl (S)-2-(N-t-butoxycarbonylamino)-4-iodobutanoate (161529-22-2)

Guidance literature:

Multi-step reaction with 2 steps

1: TEA / tetrahydrofuran / 1 h / Ambient temperature

2: 82 percent / polystyryl diphenyl phosphine-iodine complex, imidazole / CH₂Cl₂ / 1 h / Heating

With 1H-imidazole; polystyryl diphenyl phosphine-iodine; TEA; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(94)02202-M

upstream raw materials:

benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate

di-tert-butyl dicarbonate

BOC-L-aspartic acid 4-benzyl ester

(S)-3-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester

Downstream raw materials:

(3S)-benzyl 3-amino-4-iodobutanoate hydrochloride

(3S)-benzyl 3-(diphenylmethylideneamino)-4-iodobutanoate

(1R,2R)-benzyl 2-(diphenylmethylideneamino)cyclopropanecarboxylate

Boc-β³-Cys(Ac)-OBn

Refernces

• 1、 Meiresonne, Tamara,Mangelinckx, Sven,De Kimpe, Norbert. "Stereoselective synthesis of both enantiomers of trans-2- (diphenylmethylideneamino)cyclopropanecarboxylic acid using a chiral pool approach and their incorporation in dipeptides". . p. 9566 - 9571,6. Retrieved 2020/08/20.
• 2、 Caputo, Romualdo,Cassano, Ersilia,Longobardo, Luigi,Palumbo, Giovanni. "Chiral N-Protected β-Iodoamines from α-Aminoacids: a General Synthesis". . p. 167 - 168. Retrieved 2007/10/02.