(1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[2.2.1]heptan-2-one

Base Information

Chemical Name:(1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[2.2.1]heptan-2-one
CAS No.:401593-20-2
Molecular Formula:C₂₁H₂₈O₅
Molecular Weight:360.45
Hs Code.:

Synonyms:(1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[2.2.1]heptan-2-one

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Chemical Property of (1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[2.2.1]heptan-2-one

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Technology Process of (1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[2.2.1]heptan-2-one

There total 11 articles about (1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[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:

: (1R,3S,4S,5S,6R)-6-Benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-bicyclo[2.2.1]heptane-1,3-diol

: 401593-20-2
(1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[2.2.1]heptan-2-one

Guidance literature:: With dipyridinium dichromate; 4 A molecular sieve; In chloroform; at 20 ℃;
DOI:10.1016/S0040-4039(01)02032-9

Reference yield:

: 100-39-0
benzyl bromide

: 401593-20-2
(1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[2.2.1]heptan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / tetrahydrofuran; dimethylformamide

2: TBAF / dimethylformamide / 50 °C

3: pyridine / 20 °C

4: TsOH / methanol / 20 °C

5: LiAlH₄ / diethyl ether / 0 °C

6: PDC; 4 Angstroem molecular sieves / CHCl₃ / 20 °C

With lithium aluminium tetrahydride; dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)02032-9

Reference yield:

: (1R,3S,4S)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-methoxymethoxy-5-oxo-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

: 401593-20-2
(1S,4R,5R,6S)-5-Benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-methyl-bicyclo[2.2.1]heptan-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: NaBH₄ / methanol / 0 °C

2: imidazole / dimethylformamide

3: 86 percent / LDA / tetrahydrofuran / -78 - 20 °C

4: LiAlH₄ / tetrahydrofuran / 0 °C

5: NaH / tetrahydrofuran; dimethylformamide

6: TBAF / dimethylformamide / 50 °C

7: pyridine / 20 °C

8: TsOH / methanol / 20 °C

9: LiAlH₄ / diethyl ether / 0 °C

10: PDC; 4 Angstroem molecular sieves / CHCl₃ / 20 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)02032-9