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

Base Information

Chemical Name:methyl (5R,6S,7S,8R)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate
CAS No.:169220-58-0
Molecular Formula:C₃₈H₄₈N₂O₆Si
Molecular Weight:656.894
Hs Code.:

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

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

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

There total 10 articles about methyl (5R,6S,7S,8R)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-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:

: 162438-92-8
2-[(1R,2R,3S,4S)-2,3,5-tris(benzyloxy)-1,4-dihydroxypent-1-yl]-N-triphenylmethylimidazole

: 169220-58-0
methyl (5R,6S,7S,8R)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridine / 1 h / -15 °C

2.1: 0.282 g / pyridine / 2.5 h / 0 - 60 °C

3.1: 95 percent / MeOH; NaOMe / 1.5 h / 20 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -15 °C

5.1: 86 percent / NaHCO₃; 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one / CH₂Cl₂ / 4 h / 0 - 10 °C

6.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C

6.2: 85 percent / water / tetrahydrofuran; pentane / -78 - 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

7.2: CuI / tetrahydrofuran; hexane / 0.17 h / -78 °C

7.3: 88 percent / tetrahydrofuran; hexane / 0.25 h / -78 - 20 °C

8.1: 90 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

9.1: 80 percent / Ag₂CO₃ / benzene / 12 h / Heating

10.1: NaIO₄ / methanol; H₂O / 0.5 h / 20 °C

11.1: 0.0814 g / tetrahydrofuran; methanol; hexane / 0.17 h / 20 °C

With pyridine; 2,6-dimethylpyridine; methanol; sodium periodate; n-butyllithium; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tert.-butyl lithium; sodium methylate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; silver carbonate; osmium(VIII) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; pentane; benzene; 1.1: sulfonylation / 2.1: Cyclization / 3.1: Deacetylation / 4.1: silylation / 5.1: Bromination / 6.1: Metallation / 6.2: Hydrolysis / 7.1: Metallation / 7.2: complexation / 7.3: Alkylation / 8.1: hydroxylation / 9.1: Oxidation / 10.1: Oxidation / 11.1: Esterification;
DOI:10.1246/bcsj.70.427

Reference yield:

: Phenyl-methanesulfonic acid (1S,2R,3R,4R)-2,3-bis-benzyloxy-1-benzyloxymethyl-4-hydroxy-4-(1-trityl-1H-imidazol-2-yl)-butyl ester

: 169220-58-0
methyl (5R,6S,7S,8R)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 0.282 g / pyridine / 2.5 h / 0 - 60 °C

2.1: 95 percent / MeOH; NaOMe / 1.5 h / 20 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -15 °C

4.1: 86 percent / NaHCO₃; 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one / CH₂Cl₂ / 4 h / 0 - 10 °C

5.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C

5.2: 85 percent / water / tetrahydrofuran; pentane / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

6.2: CuI / tetrahydrofuran; hexane / 0.17 h / -78 °C

6.3: 88 percent / tetrahydrofuran; hexane / 0.25 h / -78 - 20 °C

7.1: 90 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

8.1: 80 percent / Ag₂CO₃ / benzene / 12 h / Heating

9.1: NaIO₄ / methanol; H₂O / 0.5 h / 20 °C

10.1: 0.0814 g / tetrahydrofuran; methanol; hexane / 0.17 h / 20 °C

With pyridine; 2,6-dimethylpyridine; methanol; sodium periodate; n-butyllithium; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tert.-butyl lithium; sodium methylate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; silver carbonate; osmium(VIII) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; pentane; benzene; 1.1: Cyclization / 2.1: Deacetylation / 3.1: silylation / 4.1: Bromination / 5.1: Metallation / 5.2: Hydrolysis / 6.1: Metallation / 6.2: complexation / 6.3: Alkylation / 7.1: hydroxylation / 8.1: Oxidation / 9.1: Oxidation / 10.1: Esterification;
DOI:10.1246/bcsj.70.427

Reference yield:

: 188476-94-0
(5R,6S,7S,8R)-6,7-bis(benzyloxy)-5-benzyloxymethyl-2-bromo-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

: 169220-58-0
methyl (5R,6S,7S,8R)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

1.2: CuI / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.3: 88 percent / tetrahydrofuran; hexane / 0.25 h / -78 - 20 °C

2.1: 90 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

3.1: 80 percent / Ag₂CO₃ / benzene / 12 h / Heating

4.1: NaIO₄ / methanol; H₂O / 0.5 h / 20 °C

5.1: 0.0814 g / tetrahydrofuran; methanol; hexane / 0.17 h / 20 °C

With sodium periodate; n-butyllithium; 4-methylmorpholine N-oxide; silver carbonate; osmium(VIII) oxide; In tetrahydrofuran; methanol; hexane; water; benzene; 1.1: Metallation / 1.2: complexation / 1.3: Alkylation / 2.1: hydroxylation / 3.1: Oxidation / 4.1: Oxidation / 5.1: Esterification;
DOI:10.1246/bcsj.70.427