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

Base Information

Chemical Name: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
CAS No.:849467-70-5
Molecular Formula:C₃₄H₃₇N₃O₆
Molecular Weight:583.684
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 81.0%

: 849467-69-2
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

: 108-24-7
acetic anhydride

: 849467-70-5
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

Guidance literature:: With pyridine; at 23 ℃; for 3h;
DOI:10.1002/hlca.200490286

Reference yield:

: 847372-42-3
methyl 3-amino-4,4-dimethoxybutanoate

: 849467-70-5
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

Guidance literature:: Multi-step reaction with 4 steps

1.1: HgCl₂ / tetrahydrofuran / 19 h / 23 °C

1.2: TsOH*H₂O / toluene / 40 h / 60 °C

2.1: 6 percent / DPPA; DBU / toluene / 22 h / 23 °C

3.1: 85 percent / Et₃N; HS-(CH₂)3-SH / methanol / 23 h / 23 °C

4.1: 81 percent / pyridine / 3 h / 23 °C

With pyridine; 1.3-propanedithiol; diphenyl-phosphinic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; mercury dichloride; In tetrahydrofuran; methanol; toluene;
DOI:10.1002/hlca.200490286

Reference yield:

: 272124-00-2
2-O-acetyl-5-amino-3,4,6-tri-O-benzyl-5-deoxy-D-gluconothiolactam

: 849467-70-5
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

Guidance literature:: Multi-step reaction with 4 steps

1.1: HgCl₂ / tetrahydrofuran / 19 h / 23 °C

1.2: TsOH*H₂O / toluene / 40 h / 60 °C

2.1: 6 percent / DPPA; DBU / toluene / 22 h / 23 °C

3.1: 85 percent / Et₃N; HS-(CH₂)3-SH / methanol / 23 h / 23 °C

4.1: 81 percent / pyridine / 3 h / 23 °C

With pyridine; 1.3-propanedithiol; diphenyl-phosphinic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; mercury dichloride; In tetrahydrofuran; methanol; toluene;
DOI:10.1002/hlca.200490286