(1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate

Base Information

Chemical Name:(1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate
CAS No.:1314025-14-3
Molecular Formula:C₂₇H₃₆O₅
Molecular Weight:440.58
Hs Code.:

Synonyms:(1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate

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Chemical Property of (1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate

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Technology Process of (1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate

There total 8 articles about (1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate 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: 76.0%

: 1314025-13-2
(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-(4-diazo-3-oxo-butyl)-3-methyltetrahydrofuran-3-yl acetate

: 1314025-14-3
(1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate

Guidance literature:: With copper(II) hexafluoroacetylacetonate; In dichloromethane; for 0.5h; Reflux; Inert atmosphere;
DOI:10.1021/ol201498g

Reference yield:

: 1314025-11-0
(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-3-methyl-2-(3-oxopropyl)-tetrahydrofuran-3-yl acetate

: 1314025-14-3
(1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 20 °C

2.1: sodium methylate / methanol / 0.25 h / 20 °C

2.2: 2 h / 20 °C

3.1: diethyl ether; dichloromethane / 1 h / 0 °C

4.1: copper(II) hexafluoroacetylacetonate / dichloromethane / 0.5 h / Reflux; Inert atmosphere

With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; sodium methylate; copper(II) hexafluoroacetylacetonate; In methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol201498g

Reference yield:

: 1314025-17-6
(2R,3R,5R)-5-[(3R,6S)-6-(benzyloxy)-3-isopropylcyclohex-1-enyl]-2-[3-(4-methoxybenzyloxy)-propyl]-3-methyltetrahydrofuran-3-yl acetate

: 1314025-14-3
(1R,2R,3R,6S,10R,11R)-6-benzyloxy-3-isopropyl-10-methyl-14-oxo-15-oxatricyclo[9.3.1.0(2,7)]-pentadec-7-en-10-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C

3.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 20 °C

4.1: sodium methylate / methanol / 0.25 h / 20 °C

4.2: 2 h / 20 °C

5.1: diethyl ether; dichloromethane / 1 h / 0 °C

6.1: copper(II) hexafluoroacetylacetonate / dichloromethane / 0.5 h / Reflux; Inert atmosphere

With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; sodium methylate; copper(II) hexafluoroacetylacetonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 2.1: Dess-Martin oxidation;
DOI:10.1021/ol201498g