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

Base Information

Chemical Name:methyl (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine-2-acetate
CAS No.:188476-91-7
Molecular Formula:C₃₂H₃₄N₂O₆
Molecular Weight:542.632
Hs Code.:

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

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

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

There total 12 articles about methyl (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydro-8-hydroxyimidazo[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: 97.0%

: 169134-69-4
methyl (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-acetate

: 188476-91-7
methyl (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine-2-acetate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1246/bcsj.70.427

Reference yield:

: 16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3
2,3,5-tri-O-benzyl-α-L-ribofuranose

: 188476-91-7
methyl (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine-2-acetate

Guidance literature:: Multi-step reaction with 13 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -5 °C

1.2: 40 percent / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

2.1: 86 percent / pyridine / 1 h / 0 °C

3.1: 98 percent / pyridine / 1.5 h / 60 °C

4.1: 95 percent / MeOH; NaOMe / 1.5 h / 20 °C

5.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -15 °C

6.1: 92 percent / NaHCO₃; 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one / CH₂Cl₂ / 4 h / 0 - 10 °C

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

7.2: 89 percent / water / tetrahydrofuran; pentane / -78 - 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

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

8.3: 88 percent / tetrahydrofuran; hexane / 0.25 h / -78 - 20 °C

9.1: 97 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

10.1: 86 percent / Ag₂CO₃ / benzene / 12 h / Heating

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

12.1: 0.0128 g / tetrahydrofuran; methanol; hexane / 0.17 h / 20 °C

13.1: 97 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; methanol; sodium periodate; n-butyllithium; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tetrabutyl ammonium fluoride; 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: Metallation / 1.2: Addition / 2.1: sulfonylation / 3.1: Cyclization / 4.1: Deacetylation / 5.1: silylation / 6.1: Bromination / 7.1: Metallation / 7.2: Hydrolysis / 8.1: Metallation / 8.2: complexation / 8.3: Alkylation / 9.1: hydroxylation / 10.1: Oxidation / 11.1: Oxidation / 12.1: Esterification / 13.1: desilylation;
DOI:10.1246/bcsj.70.427

Reference yield:

: 162438-96-2
2-[(1S,2R,3S,4S)-2,3,5-tris(benzyloxy)-4-benzylsulfonyloxy-1-hydroxypent-1-yl]-N-triphenylmethylimidazole

: 188476-91-7
methyl (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine-2-acetate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / pyridine / 1.5 h / 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: 92 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: 89 percent / water / tetrahydrofuran; pentane / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.17 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: 97 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

8.1: 86 percent / Ag₂CO₃ / benzene / 12 h / Heating

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

10.1: 0.0128 g / tetrahydrofuran; methanol; hexane / 0.17 h / 20 °C

11.1: 97 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; methanol; sodium periodate; n-butyllithium; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tetrabutyl ammonium fluoride; 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 / 11.1: desilylation;
DOI:10.1246/bcsj.70.427