benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester

Base Information

Chemical Name:benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester
CAS No.:922163-70-0
Molecular Formula:C₄₂H₄₈I₂N₂O₆Si
Molecular Weight:958.747
Hs Code.:

benzoic acid 2,3,5-tris-benzyloxy-4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1<i>H</i>-imidazol-2-yl)-pentyl ester

Synonyms:benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester

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Chemical Property of benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester

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Technology Process of benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester

There total 10 articles about benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester 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: 90.0%

: 922163-69-7
benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(1H-imidazol-2-yl)-pentyl ester

: 922163-70-0
benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester

Guidance literature:: With N-iodo-succinimide; In acetonitrile; at 20 ℃; for 12h;
DOI:10.1021/ja066743n

Reference yield:

: 922163-66-4
(2S,3S,4S)-2,3,5-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentanal

: 922163-70-0
benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -20 - 20 °C

1.2: tetrahydrofuran / 1 h / -78 - 20 °C

2.1: trifluoroacetic acid / CHCl₃ / 0.42 h / 20 °C

3.1: 0.86 g / 4-N,N-dimethylaminopyridine; pyridine / 0.5 h / 20 °C

4.1: 90 percent / N-iodosuccinimide / acetonitrile / 12 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; n-butyllithium; trifluoroacetic acid; In tetrahydrofuran; hexane; chloroform; acetonitrile;
DOI:10.1021/ja066743n

Reference yield:

: 922499-10-3
(2R,3S,4S)-2,3,5-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentan-1-ol

: 922163-70-0
benzoic acid 2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-diiodo-1H-imidazol-2-yl)-pentyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -60 - 0 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -20 - 20 °C

2.2: tetrahydrofuran / 1 h / -78 - 20 °C

3.1: trifluoroacetic acid / CHCl₃ / 0.42 h / 20 °C

4.1: 0.86 g / 4-N,N-dimethylaminopyridine; pyridine / 0.5 h / 20 °C

5.1: 90 percent / N-iodosuccinimide / acetonitrile / 12 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform; acetonitrile; 1.1: Swern oxidation;
DOI:10.1021/ja066743n