(1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-one

Base Information

Chemical Name:(1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-one
CAS No.:1361049-63-9
Molecular Formula:C₂₂H₃₀O₆Si
Molecular Weight:418.562
Hs Code.:

Synonyms:(1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-one

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Chemical Property of (1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-one

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Technology Process of (1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-one

There total 9 articles about (1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-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: 53.0%

: 1361049-62-8
(5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(benzoyloxymethyl)furan-2(5H)-one

: 1361049-74-2
(1R,3R,4R,6R,7R)-6-benzoyloxymethyl-3-(tert-butyldimethylsilyloxy)-7-hydroxy-9-oxa-tricyclo[4.3.0.0(4,7)]nonan-8-one

: 1361049-63-9
(1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-one

Guidance literature:: (5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(benzoyloxymethyl)furan-2(5H)-one; In acetone; acetonitrile; for 2h; Irradiation;

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 16h; under 760.051 Torr;
DOI:10.1002/anie.201106889

Reference yield:

: 1361049-72-0
(5R,2'R)-3-(benzyloxy)-5-[2'-(tert-butyldimethylsilyloxy)but-3'-enyl]-4-(methoxycarbonyl)furan-2(5H)-one

: 1361049-74-2
(1R,3R,4R,6R,7R)-6-benzoyloxymethyl-3-(tert-butyldimethylsilyloxy)-7-hydroxy-9-oxa-tricyclo[4.3.0.0(4,7)]nonan-8-one

: 1361049-63-9
(1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: barium hydroxide octahydrate / tetrahydrofuran; water / 60 h / 20 °C

2.1: 4-methyl-morpholine; methyl chloroformate / tetrahydrofuran / 0.5 h / -10 °C

2.2: 0.5 h / 0 °C

3.1: dmap; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C

4.1: acetone; acetonitrile / 2 h / Irradiation

4.2: 16 h / 20 °C / 760.05 Torr

With 4-methyl-morpholine; dmap; barium hydroxide octahydrate; triethylamine; methyl chloroformate; In tetrahydrofuran; dichloromethane; water; acetone; acetonitrile;
DOI:10.1002/anie.201106889

Reference yield:

: 1361049-71-9
C₁₆H₂₆O₆Si

: 1361049-74-2
(1R,3R,4R,6R,7R)-6-benzoyloxymethyl-3-(tert-butyldimethylsilyloxy)-7-hydroxy-9-oxa-tricyclo[4.3.0.0(4,7)]nonan-8-one

: 1361049-63-9
(1R,4R,6R,7R,9R)-9-benzoyloxymethyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2-oxa-tricyclo[4.2.1.0(4,9)]nonan-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

1.2: 21 h / 20 °C

2.1: barium hydroxide octahydrate / tetrahydrofuran; water / 60 h / 20 °C

3.1: 4-methyl-morpholine; methyl chloroformate / tetrahydrofuran / 0.5 h / -10 °C

3.2: 0.5 h / 0 °C

4.1: dmap; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C

5.1: acetone; acetonitrile / 2 h / Irradiation

5.2: 16 h / 20 °C / 760.05 Torr

With 4-methyl-morpholine; dmap; barium hydroxide octahydrate; sodium hydride; triethylamine; methyl chloroformate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;
DOI:10.1002/anie.201106889