Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester

Base Information

Chemical Name:Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester
CAS No.:502442-85-5
Molecular Formula:C₂₅H₄₀O₅Si
Molecular Weight:448.675
Hs Code.:

Synonyms:Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester

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Chemical Property of Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester

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Technology Process of Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester

There total 14 articles about Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester 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: 96.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

: 502442-85-5
Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1016/S0040-4039(98)01385-9

Reference yield:

: 3-Methoxymethoxy-cyclopent-2-enone

: 502442-85-5
Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester

Guidance literature:: Multi-step reaction with 11 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

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

Reference yield:

: 213816-80-9
[(1R,2R,3R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxymethoxy-2-methyl-bicyclo[2.2.1]hept-2-yl]-methanol

: 502442-85-5
Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-bicyclo[2.2.1]hept-2-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / NaH / dimethylformamide / 12 h / 20 °C

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

3: 99 percent / pyridine / 10 h / 20 °C

4: 80 percent / CH₃COOH / H₂O / 12 h / 65 °C

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

6: 13 g / NaBH₄ / methanol; H₂O / 0.08 h / 0 °C

7: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C

With pyridine; 1H-imidazole; ammonium sulfate; sodium tetrahydroborate; sodium periodate; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)01474-6