(-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-one

Base Information

Chemical Name:(-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-one
CAS No.:1370458-44-8
Molecular Formula:C₁₉H₂₂O₅
Molecular Weight:330.381
Hs Code.:

Synonyms:(-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-one

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Chemical Property of (-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-one

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Technology Process of (-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-one

There total 12 articles about (-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-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: 89.0%

: 1370458-42-6
(-)-(2R,4aR,7S,8R,8aR)-2,7-ethano-2,8-dimethyl-8a-methoxyhexahydropyrano[4.3-b]pyran-5(7H)-one

: 98-88-4
benzoyl chloride

: 1370458-44-8
(-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-one

Guidance literature:: With dmap; In dichloromethane; at 0 - 20 ℃; for 18h; Inert atmosphere;
DOI:10.1021/ol300615w

Reference yield:

: 1370458-47-1
C₁₁H₂₁NO₃

: 1370458-44-8
(-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1H-imidazole / dichloromethane / 5 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; toluene / 3 h / -78 °C / Inert atmosphere

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

3.2: 5 h / 0 - 20 °C / Inert atmosphere

4.1: Otera's catalyst / toluene / 13 h / 110 °C

5.1: Dess-Martin periodane / dichloromethane / 6 h / 0 °C / Inert atmosphere

6.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 72 h / 100 °C / Inert atmosphere

7.1: water; trifluoroacetic acid / dichloromethane / 4 h / 0 °C / Inert atmosphere

8.1: 2-chloro-1-methyl-pyridinium iodide; sodium hydrogencarbonate / dichloromethane / 48 h / 20 °C / Inert atmosphere

9.1: hydrogenchloride / 0.17 h / 20 °C / Inert atmosphere

10.1: dmap / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; Otera's catalyst; 2,6-di-tert-butyl-4-methyl-phenol; 2-chloro-1-methyl-pyridinium iodide; water; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; toluene; 5.1: Dess-Martin oxidation / 6.1: Intra-molecular hetero-Diels-Alder reaction;
DOI:10.1021/ol300615w

Reference yield:

: 1370458-38-0
(+)-(1R,4R,5R)-1,5-dimethyl-4-triethylsilanyloxy-10-oxa-bicyclo[4.3.1]dec-6-ene-7-carboxylic acid p-methoxybenzyl ester

: 1370458-44-8
(-)-(2R,4aR,7S,8R,8aS)-2,7-ethano-8a-benzocycloxy-2,8-dimethylhexahydropyrano[4.3-b]pyran-5(7H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: water; trifluoroacetic acid / dichloromethane / 4 h / 0 °C / Inert atmosphere

2: 2-chloro-1-methyl-pyridinium iodide; sodium hydrogencarbonate / dichloromethane / 48 h / 20 °C / Inert atmosphere

3: hydrogenchloride / 0.17 h / 20 °C / Inert atmosphere

4: dmap / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; dmap; 2-chloro-1-methyl-pyridinium iodide; water; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ol300615w