(Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione

Base Information

Chemical Name:(Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione
CAS No.:272787-07-2
Molecular Formula:C₁₆H₂₂O₆
Molecular Weight:310.347
Hs Code.:

Synonyms:(Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione

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Chemical Property of (Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione

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Technology Process of (Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione

There total 8 articles about (Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione 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: 43.0%

: 272787-05-0
(3R,3aR,7aS)-3-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3a-hydroxy-7a-trimethylsilanyloxy-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one

: 272787-07-2
(Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione

: (Z)-(3S,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione

Guidance literature:: (3R,3aR,7aS)-3-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3a-hydroxy-7a-trimethylsilanyloxy-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one; With iodine; mercury(II) oxide; In benzene; Irradiation; reflux;

With sodium cyanoborohydride; In acetic acid; at 13 - 20 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(02)00037-6

Reference yield:

: 6614-52-4
5,6-O-cyclohexylidene-L-ascorbic acid

: 272787-07-2
(Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: aq. NaOH / tetrahydrofuran / 10 h / 20 °C / pH 7 - 8

2.1: 46 percent / imidazole / tetrahydrofuran / 2 h / 20 °C

3.1: I₂; Zn / tetrahydrofuran / 0.17 h

3.2: 94 percent / tetrahydrofuran / 1 h

4.1: 70 percent / Grubbs' catalyst / toluene / 20 h / 60 - 70 °C

5.1: yellow HgO; I₂ / benzene / Irradiation; reflux

5.2: 43 percent / NaCNBH₃ / acetic acid / 0.33 h / 13 - 20 °C

With 1H-imidazole; sodium hydroxide; Grubbs catalyst first generation; iodine; mercury(II) oxide; zinc; In tetrahydrofuran; toluene; benzene;
DOI:10.1016/S0040-4020(02)00037-6

Reference yield:

: (R)-3-Allyl-5-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-furan-2,4-dione

: 272787-07-2
(Z)-(3R,9R)-9-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-hydroxy-4,7-dihydro-3H-oxonine-2,8-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: 46 percent / imidazole / tetrahydrofuran / 2 h / 20 °C

2.1: I₂; Zn / tetrahydrofuran / 0.17 h

2.2: 94 percent / tetrahydrofuran / 1 h

3.1: 70 percent / Grubbs' catalyst / toluene / 20 h / 60 - 70 °C

4.1: yellow HgO; I₂ / benzene / Irradiation; reflux

4.2: 43 percent / NaCNBH₃ / acetic acid / 0.33 h / 13 - 20 °C

With 1H-imidazole; Grubbs catalyst first generation; iodine; mercury(II) oxide; zinc; In tetrahydrofuran; toluene; benzene;
DOI:10.1016/S0040-4020(02)00037-6