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

Base Information

Chemical Name:(1R,3S,4S,5R,6R)-6-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-bicyclo[2.2.1]heptane-1,3-diol
CAS No.:502442-86-6
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

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

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Chemical Property of (1R,3S,4S,5R,6R)-6-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-bicyclo[2.2.1]heptane-1,3-diol

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Technology Process of (1R,3S,4S,5R,6R)-6-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-bicyclo[2.2.1]heptane-1,3-diol

There total 15 articles about (1R,3S,4S,5R,6R)-6-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-bicyclo[2.2.1]heptane-1,3-diol 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: 100.0%

: 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

: 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

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(02)01474-6

Reference yield:

: 3-Methoxymethoxy-cyclopent-2-enone

: 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

Guidance literature:: Multi-step reaction with 12 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

With pyridine; 1H-imidazole; ammonium sulfate; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; 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:

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With 1H-imidazole; potassium carbonate; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)01474-6