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

Base Information

• Chemical Name: Imidazo[1,2-a]pyridine-2-acetic acid, 5,6,7,8-tetrahydro-6,7-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-8- [[tris(1-methylethyl)silyl]oxy]-, methyl ester, (5R,6R,7S,8R)-
• CAS No.: 849467-64-7
• Molecular Formula: C41H54N2O6Si
• Molecular Weight: 698.975
• Mol file: 849467-64-7.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Imidazo[1,2-a]pyridine-2-acetic acid, 5,6,7,8-tetrahydro-6,7-bis(phenylmethoxy)-5-[(phenylmethoxy)methyl]-8- [[tris(1-methylethyl)silyl]oxy]-, methyl ester, (5R,6R,7S,8R)- 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: 29.0%

5-amino-3,4,6-tri-O-benzyl-5-deoxy-2-O-(triisopropylsilyl)-D-glucono-1,5-thiolactam (848782-16-1) + methyl 3-amino-4,4-dimethoxybutanoate (847372-42-3) → methyl (5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-(triisopropylsilyloxy)-imidazo[1,2-a]pyridine-2-acetate (849467-63-6) + methyl (5R,6R,7S,8R)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-(triisopropylsilyloxy)-imidazo[1,2-a]pyridine-2-acetate (849467-64-7)

Guidance literature:

5-amino-3,4,6-tri-O-benzyl-5-deoxy-2-O-(triisopropylsilyl)-D-glucono-1,5-thiolactam; methyl 3-amino-4,4-dimethoxybutanoate; With mercury dichloride; In tetrahydrofuran; at 22 ℃; for 12h;

With toluene-4-sulfonic acid; In toluene; at 60 ℃; for 40h;

DOI:10.1002/hlca.200490286

Reference yield: 93.0%

methyl (5R,6R,7S,8R)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-(triisopropylsilyloxy)-imidazo[1,2-a]pyridine-2-acetate (849467-64-7) → methyl (5R,6R,7S,8R)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine-2-acetate (849467-66-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1002/hlca.200490286

Reference yield:

methyl (5R,6R,7S,8R)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-(triisopropylsilyloxy)-imidazo[1,2-a]pyridine-2-acetate (849467-64-7) → methyl (5R,6R,7S,8S)-8-amino-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate (849467-69-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / Bu₄NF / tetrahydrofuran / 2 h / 0 °C

2: 69 percent / DPPA; DBU / toluene / 5 h / 23 °C

3: 85 percent / Et₃N; HS-(CH₂)3-SH / methanol / 23 h / 23 °C

With 1.3-propanedithiol; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; toluene;

DOI:10.1002/hlca.200490286

upstream raw materials:

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

methyl 3-amino-4,4-dimethoxybutanoate

Downstream raw materials:

methyl (5R,6R,7S,8R)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine-2-acetate

methyl (5R,6R,7S,8S)-8-amino-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate

methyl (5R,6R,7S,8S)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate

methyl (5R,6R,7S,8S)-8-acetamido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate