(2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

Base Information

Chemical Name:(2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate
CAS No.:1241959-36-3
Molecular Formula:C₃₄H₄₅NO₆Si
Molecular Weight:591.82
Hs Code.:

Synonyms:(2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

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Chemical Property of (2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

Chemical Property:

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Technology Process of (2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

There total 19 articles about (2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate 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: 92.0%

: 1241959-32-9
tert-butyl (3R,6R)-6-((benzyloxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate

: 1241959-36-3
(2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

Guidance literature:: With potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; at 0 ℃;
DOI:10.1021/ol101556k

Reference yield:

: C₁₅H₂₀O₃

: 1241959-36-3
(2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: potassium hexacyanoferrate(III); potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; osmium(VIII) oxide; methanesulfonamide / tert-butyl alcohol; water / 24 h / 0 °C

2: triethylamine; dmap / dichloromethane / 5 h

3: sodium azide / N,N-dimethyl-formamide / 18 h / 80 °C

4: palladium(II) hydroxide; hydrogen / methanol / 3 h / 20 °C / 1551.49 Torr

5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C

6: triethylamine; dmap / tetrahydrofuran / 20 °C

7: triphenylphosphine; 1H-imidazole; iodine / toluene / 0.5 h / 120 °C / Inert atmosphere

8: selenium(IV) oxide / 1,4-dioxane / 3 h / Reflux

9: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Reflux

10: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0 °C

11: dmap; 1H-imidazole / dichloromethane / 15 h

12: sodium periodate; ruthenium trichloride / water; ethyl acetate; acetonitrile

With 1H-imidazole; dmap; selenium(IV) oxide; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; methanesulfonamide; cerium(III) chloride heptahydrate; hydrogen; iodine; palladium(II) hydroxide; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1: |Sharpless Asymmetric Epoxidation;
DOI:10.1039/c4ra04558k

Reference yield:

: Methanesulfonic acid (R)-2-benzyloxy-1-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

: 1241959-36-3
(2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: sodium azide / N,N-dimethyl-formamide / 18 h / 80 °C

2: palladium(II) hydroxide; hydrogen / methanol / 3 h / 20 °C / 1551.49 Torr

3: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C

4: triethylamine; dmap / tetrahydrofuran / 20 °C

5: triphenylphosphine; 1H-imidazole; iodine / toluene / 0.5 h / 120 °C / Inert atmosphere

6: selenium(IV) oxide / 1,4-dioxane / 3 h / Reflux

7: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Reflux

8: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0 °C

9: dmap; 1H-imidazole / dichloromethane / 15 h

10: sodium periodate; ruthenium trichloride / water; ethyl acetate; acetonitrile

With 1H-imidazole; dmap; selenium(IV) oxide; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; sodium azide; cerium(III) chloride heptahydrate; hydrogen; iodine; palladium(II) hydroxide; triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1039/c4ra04558k