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

Base Information

Chemical Name:(5R,6R,7S,8S)-6-amino-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
CAS No.:916495-09-5
Molecular Formula:C₂₉H₃₁N₃O₃
Molecular Weight:469.583
Hs Code.:

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

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

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

There total 6 articles about (5R,6R,7S,8S)-6-amino-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 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: 42.0%

: Trifluoro-methanesulfonic acid (5R,6S,7R,8S)-7,8-bis-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-6-yl ester

: (7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-7,8-dihydroimidazo[1,2-a]pyridine

: 916495-09-5
(5R,6R,7S,8S)-6-amino-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Guidance literature:: Trifluoro-methanesulfonic acid (5R,6S,7R,8S)-7,8-bis-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-6-yl ester; With sodium azide; In N,N-dimethyl-formamide; for 0.5h;

With hydrogen; Lindlar's catalyst; In tetrahydrofuran; for 20h; under 750.06 Torr;
DOI:10.1002/hlca.200690191

Reference yield:

: 916494-99-0
5-amino-2,3-di-O-benzyl-4,6-O-benzylidene-5-deoxy-D-galactono-1,5-lactam

: 916495-09-5
(5R,6R,7S,8S)-6-amino-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / 4A MS; Et₃SiH; TfOH / CH₂Cl₂ / 1 h / -78 °C

2.1: 99 percent / pyridine / 2 h

3.1: 90 percent / Lawesson's reagent / toluene / 0.5 h / 80 °C

4.1: Hg(OAc)2 / tetrahydrofuran / 2 h

4.2: 78 percent / TsOH*H₂O / toluene; H₂O / 24 h / 75 °C

5.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

6.1: NaN₃ / dimethylformamide / 0.5 h

6.2: 42 percent / H₂ / Pd/CaCO₃ / tetrahydrofuran / 20 h / 750.06 Torr

With Lawessons reagent; pyridine; triethylsilane; sodium azide; trifluorormethanesulfonic acid; mercury(II) diacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.200690191

Reference yield:

: 916495-00-6
5-amino-2,3,6-tri-O-benzyl-5-deoxy-D-galactono-1,5-lactam

: 916495-09-5
(5R,6R,7S,8S)-6-amino-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / pyridine / 2 h

2.1: 90 percent / Lawesson's reagent / toluene / 0.5 h / 80 °C

3.1: Hg(OAc)2 / tetrahydrofuran / 2 h

3.2: 78 percent / TsOH*H₂O / toluene; H₂O / 24 h / 75 °C

4.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

5.1: NaN₃ / dimethylformamide / 0.5 h

5.2: 42 percent / H₂ / Pd/CaCO₃ / tetrahydrofuran / 20 h / 750.06 Torr

With Lawessons reagent; pyridine; sodium azide; mercury(II) diacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.200690191