(1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one

Base Information

Chemical Name:(1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one
CAS No.:226718-71-4
Molecular Formula:C₂₃H₃₆O₄Si
Molecular Weight:404.622
Hs Code.:

Synonyms:(1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one

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Chemical Property of (1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one

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Technology Process of (1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one

There total 16 articles about (1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one 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: 90.0%

: 502442-86-6
(1R,3S,4S,5R,6R)-6-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-bicyclo[2.2.1]heptane-1,3-diol

: 226718-71-4
(1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one

Guidance literature:: With 4 Angstroem MS; pyridinium chlorochromate; In dichloromethane; Ambient temperature;
DOI:10.1016/S0040-4039(98)01385-9

Reference yield:

: 3-Methoxymethoxy-cyclopent-2-enone

: 226718-71-4
(1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one

Guidance literature:: Multi-step reaction with 13 steps

1: 69 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / -78 °C

2: 100 percent / NaBH₄ / methanol / 0.25 h / 0 °C

3: 100 percent / imidazole / dimethylformamide / 10 h / 20 °C

4: 99 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

5: 94 percent / NaH / dimethylformamide / 12 h / 20 °C

6: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

7: 99 percent / pyridine / 10 h / 20 °C

8: 80 percent / CH₃COOH / H₂O / 12 h / 65 °C

9: NaIO₄; (NH₄)2SO₄ / methanol; H₂O / 0.25 h / 0 °C

10: 13 g / NaBH₄ / methanol; H₂O / 0.08 h / 0 °C

11: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C

12: 100 percent / K₂CO₃ / methanol / 2 h / 20 °C

13: 90 percent / pyridinium chlorochromate; molecular sieves 4 Amgstroem / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; ammonium sulfate; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)01474-6

Reference yield:

: 213816-83-2
Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-4-hydroxy-6-hydroxymethyl-5-methyl-bicyclo[2.2.1]hept-2-yl ester

: 226718-71-4
(1S,4R,5R,6R)-5-(benzyloxy)methyl-6-((tert-butyldimethylsilanyl)oxymethyl)-4-hydroxy-5-methylbicyclo[2.2.1]heptan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C

2: 100 percent / K₂CO₃ / methanol / 2 h / 20 °C

3: 90 percent / pyridinium chlorochromate; molecular sieves 4 Amgstroem / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; 4 A molecular sieve; potassium carbonate; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)01474-6