Imidazo[1,2-a]pyridine, 5,6,7,8-tetrahydro-6,7-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-8- [[tris(1-methylethyl)silyl]oxy]-, (5R,6R,7S,8S)-

Base Information

• Chemical Name: Imidazo[1,2-a]pyridine, 5,6,7,8-tetrahydro-6,7-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-8- [[tris(1-methylethyl)silyl]oxy]-, (5R,6R,7S,8S)-
• CAS No.: 848782-17-2
• Molecular Formula: C38H50N2O4Si
• Molecular Weight: 626.912
• Mol file: 848782-17-2.mol

Synonyms:

Chemical Property of Imidazo[1,2-a]pyridine, 5,6,7,8-tetrahydro-6,7-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-8- [[tris(1-methylethyl)silyl]oxy]-, (5R,6R,7S,8S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Imidazo[1,2-a]pyridine, 5,6,7,8-tetrahydro-6,7-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-8- [[tris(1-methylethyl)silyl]oxy]-, (5R,6R,7S,8S)-

There total 1 articles about Imidazo[1,2-a]pyridine, 5,6,7,8-tetrahydro-6,7-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-8- [[tris(1-methylethyl)silyl]oxy]-, (5R,6R,7S,8S)- 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%

5-amino-3,4,6-tri-O-benzyl-5-deoxy-2-O-(triisopropylsilyl)-D-glucono-1,5-thiolactam (848782-16-1) + 2,2-dimethoxyethylamine (22483-09-6) → (5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-(triisopropylsilyl)imidazo[1,2-a]pyridine (848782-17-2)

Guidance literature:

5-amino-3,4,6-tri-O-benzyl-5-deoxy-2-O-(triisopropylsilyl)-D-glucono-1,5-thiolactam; 2,2-dimethoxyethylamine; With mercury(II) diacetate; In tetrahydrofuran;

With water; toluene-4-sulfonic acid; In toluene;

DOI:10.1039/b612154c

Reference yield: 88.0%

(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-(triisopropylsilyl)imidazo[1,2-a]pyridine (848782-17-2) → (5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2,3-diiodo-5,6,7,8-tetrahydro-8-[(triisopropylsilyl)oxy]-imidazo[1,2-a]pyridine (917109-68-3)

Guidance literature:

With N-iodo-succinimide; In N,N-dimethyl-formamide; at 80 ℃; for 6h;

DOI:10.1039/b612154c

Reference yield:

(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-(triisopropylsilyl)imidazo[1,2-a]pyridine (848782-17-2) → (5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide (917109-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / N-iodosuccinimide / dimethylformamide / 6 h / 80 °C

2.1: 88 percent / EtMgBr / tetrahydrofuran / 0.17 h / 0 °C

3.1: EtMgBr / tetrahydrofuran / 0.17 h / 0 °C

3.2: 81 percent / tetrahydrofuran / 2.5 h / 0 - 23 °C

4.1: 93 percent / Bu₄NF / tetrahydrofuran / 3 h / 0 °C

With N-iodo-succinimide; ethylmagnesium bromide; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b612154c

upstream raw materials:

5-amino-3,4,6-tri-O-benzyl-5-deoxy-2-O-(triisopropylsilyl)-D-glucono-1,5-thiolactam

2,2-dimethoxyethylamine

Downstream raw materials:

(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2,3-diiodo-5,6,7,8-tetrahydro-8-[(triisopropylsilyl)oxy]-imidazo[1,2-a]pyridine

(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-iodo-5,6,7,8-tetrahydro-8-[(triisopropylsilyl)oxy]-imidazo[1,2-a]pyridine

(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-N-phenyl-8-[(triisopropylsilyl)oxy]imidazo[1,2-a]pyridine-2-carboxamide