(1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol

Base Information

Chemical Name:(1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol
CAS No.:401593-24-6
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

Synonyms:(1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol

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Chemical Property of (1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol

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Technology Process of (1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol

There total 14 articles about (1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol 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%

: (1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-4-hydroxy-1-methoxy-1,5-dimethyl-hexahydro-cyclopenta[c]pyran-6-one

: 401593-24-6
(1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol

Guidance literature:: (1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-4-hydroxy-1-methoxy-1,5-dimethyl-hexahydro-cyclopenta[c]pyran-6-one; With hydrazine; In diethylene glycol; at 130 ℃;

With potassium hydroxide; at 205 ℃;
DOI:10.1016/S0040-4039(01)02032-9

Reference yield:

: 100-39-0
benzyl bromide

: 401593-24-6
(1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH / tetrahydrofuran; dimethylformamide

2.1: TBAF / dimethylformamide / 50 °C

3.1: pyridine / 20 °C

4.1: TsOH / methanol / 20 °C

5.1: LiAlH₄ / diethyl ether / 0 °C

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

7.1: 92 percent / K₂CO₃ / methanol / 40 °C

8.1: 98 percent / TsOH / 20 °C

9.1: H₂NNH₂ / bis-(2-hydroxy-ethyl) ether / 130 °C

9.2: 92 percent / KOH / 205 °C

With lithium aluminium tetrahydride; dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; hydrazine; In tetrahydrofuran; pyridine; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide; diethylene glycol; 9.1: Wolff-Kishner reduction;
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

: 401593-24-6
(1S,4R,4aS,5R,7aR)-5-Benzyloxymethyl-1-methoxy-1,5-dimethyl-octahydro-cyclopenta[c]pyran-4-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: NaBH₄ / methanol / 0 °C

2.1: imidazole / dimethylformamide

3.1: 86 percent / LDA / tetrahydrofuran / -78 - 20 °C

4.1: LiAlH₄ / tetrahydrofuran / 0 °C

5.1: NaH / tetrahydrofuran; dimethylformamide

6.1: TBAF / dimethylformamide / 50 °C

7.1: pyridine / 20 °C

8.1: TsOH / methanol / 20 °C

9.1: LiAlH₄ / diethyl ether / 0 °C

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

11.1: 92 percent / K₂CO₃ / methanol / 40 °C

12.1: 98 percent / TsOH / 20 °C

13.1: H₂NNH₂ / bis-(2-hydroxy-ethyl) ether / 130 °C

13.2: 92 percent / KOH / 205 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; hydrazine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide; diethylene glycol; 13.1: Wolff-Kishner reduction;
DOI:10.1016/S0040-4039(01)02032-9