(5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Base Information

Chemical Name:(5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
CAS No.:911386-21-5
Molecular Formula:C₃₅H₄₄N₂O₄Si
Molecular Weight:584.831
Hs Code.:

Synonyms:(5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

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Chemical Property of (5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

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Technology Process of (5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

There total 7 articles about (5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]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: 66.0%

: 911386-20-4
(5R,6S,7S,8S)-7,8-bis(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol

: 100-39-0
benzyl bromide

: 911386-21-5
(5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Guidance literature:: (5R,6S,7S,8S)-7,8-bis(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

benzyl bromide; In N,N-dimethyl-formamide; for 4h;
DOI:10.1002/hlca.200690137

Reference yield:

: 896447-96-4
5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-lactam

: 911386-21-5
(5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / pyridine / 6 h / 0 °C

2.1: 85 percent / Lawesson's reagent / toluene / 0.5 h / 80 °C

3.1: Hg(OAc)2 / tetrahydrofuran / 2 h / 0 °C

4.1: TsOH*H₂O / H₂O; toluene / 24 h / 75 °C

5.1: 300 mg / Et₃N; 4-(dimethylamino)pyridine / dimethylformamide / 16 h

6.1: NaH / dimethylformamide / 0.17 h / 0 °C

6.2: 66 percent / dimethylformamide / 4 h

With Lawessons reagent; pyridine; dmap; mercury(II) diacetate; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.200690137

Reference yield:

: (5R,6S,7S,8S)-7,8-Bis-benzyloxy-5-hydroxymethyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-6-ol

: 911386-21-5
(5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 300 mg / Et₃N; 4-(dimethylamino)pyridine / dimethylformamide / 16 h

2.1: NaH / dimethylformamide / 0.17 h / 0 °C

2.2: 66 percent / dimethylformamide / 4 h

With dmap; sodium hydride; triethylamine; In N,N-dimethyl-formamide;
DOI:10.1002/hlca.200690137