(5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[1,2-a]pyridine

Base Information

Chemical Name:(5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[1,2-a]pyridine
CAS No.:188476-90-6
Molecular Formula:C₃₈H₅₀N₂O₆Si
Molecular Weight:658.91
Hs Code.:

Synonyms:(5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[1,2-a]pyridine

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Chemical Property of (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[1,2-a]pyridine

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Technology Process of (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[1,2-a]pyridine

There total 8 articles about (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[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: 97.0%

: 169134-66-1
(5R,6S,7S,8S)-2-allyl-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

: 188476-90-6
(5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[1,2-a]pyridine

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; water; for 4h;
DOI:10.1016/00404-0399(50)1361-K

Reference yield:

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

: 188476-90-6
(5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 7 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

With pyridine; 2,6-dimethylpyridine; methanol; n-butyllithium; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tert.-butyl lithium; sodium methylate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; hexane; dichloromethane; water; pentane; 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;
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

: 188476-90-6
(5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-2-(2,3-dihydroxypropyl)imidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 9 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

With pyridine; 2,6-dimethylpyridine; methanol; n-butyllithium; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; tert.-butyl lithium; sodium methylate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; hexane; dichloromethane; water; pentane; 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;
DOI:10.1246/bcsj.70.427