(5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid

Base Information

Chemical Name:(5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid
CAS No.:125011-38-3
Molecular Formula:C₂₇H₂₈F₂O₉
Molecular Weight:534.511
Hs Code.:

(5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid

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Chemical Property of (5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid

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Technology Process of (5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid

There total 15 articles about (5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid 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:

: 98-00-0,25212-86-6,93793-62-5
(2-furyl)methyl alcohol

: 125011-38-3
(5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 1) Br₂ / 1) Et₂O; 2) methoxymethylation

2: water, Dowex 50x / acetone / cation exchange resin Dowex 50x

3: benzene / Ambient temperature

4: 71 percent / n-BuLi / tetrahydrofuran / -78 - 25 °C

5: 92 percent / i-Bu₂AlH

6: 22.5 percent / 4,4'-thiobis(2-t-butyl-6-methylphenol) / chlorobenzene / 10 h / 140 - 143 °C

8: 78 percent / LiBF₄ / acetonitrile; H₂O / Heating

9: PDC

10: NaClO₂, 2-methyl-2-butene

With sodium chlorite; dipyridinium dichromate; lithium tetrafluoroborate; n-butyllithium; 2-methyl-but-2-ene; Dowex 50X; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; water; bromine; diisobutylaluminium hydride; In tetrahydrofuran; water; chlorobenzene; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)99656-4

Reference yield:

: 125029-04-1
α-hydroxy-γ-methylenetetronate

: 125011-38-3
(5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / Et₃N, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

2: 22.5 percent / 4,4'-thiobis(2-t-butyl-6-methylphenol) / chlorobenzene / 10 h / 140 - 143 °C

4: 78 percent / LiBF₄ / acetonitrile; H₂O / Heating

5: PDC

6: NaClO₂, 2-methyl-2-butene

With sodium chlorite; dipyridinium dichromate; lithium tetrafluoroborate; 2-methyl-but-2-ene; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; water; chlorobenzene; acetonitrile;
DOI:10.1016/S0040-4039(00)99656-4

Reference yield:

: 109788-65-0
4-methoxy-5-methylidene-2(5H)-furanone

: 125011-38-3
(5R,6S,9S)-3-(2,4-Difluoro-benzoyloxy)-6-[(E)-3-(2,2-dimethyl-propionyloxy)-propenyl]-4-methoxy-9-methyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-diene-8-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 1) LiN(i-Pr)2; 2) B(OMe)3, H₂O₂ / 1) THF, -90 deg C

2: 78 percent / Et₃N, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

3: 22.5 percent / 4,4'-thiobis(2-t-butyl-6-methylphenol) / chlorobenzene / 10 h / 140 - 143 °C

5: 78 percent / LiBF₄ / acetonitrile; H₂O / Heating

6: PDC

7: NaClO₂, 2-methyl-2-butene

With sodium chlorite; dipyridinium dichromate; lithium tetrafluoroborate; 2-methyl-but-2-ene; Trimethyl borate; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; dihydrogen peroxide; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In dichloromethane; water; chlorobenzene; acetonitrile;
DOI:10.1016/S0040-4039(00)99656-4