(-)-8-epi-9-deoxygoniopypyrone

Base Information

Chemical Name:(-)-8-epi-9-deoxygoniopypyrone
CAS No.:252273-45-3
Molecular Formula:C₁₃H₁₄O₄
Molecular Weight:234.252
Hs Code.:

Synonyms:(-)-8-epi-9-deoxygoniopypyrone

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Chemical Property of (-)-8-epi-9-deoxygoniopypyrone

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Technology Process of (-)-8-epi-9-deoxygoniopypyrone

There total 12 articles about (-)-8-epi-9-deoxygoniopypyrone 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: 94.0%

: 220384-92-9
(1R,5R,7S,8S)-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

: 252273-45-3
(-)-8-epi-9-deoxygoniopypyrone

Guidance literature:: With titanium tetrachloride; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1016/S0040-4039(98)02269-2

Reference yield:

: (E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-phenyl-but-2-enoic acid ethyl ester

: 252273-45-3
(-)-8-epi-9-deoxygoniopypyrone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 36 h / 20 °C

2.1: 95 percent / camphorsulfonic acid / benzene / 1 h / Heating

3.1: 99 percent / LiAlH₄ / diethyl ether / 0.08 h / 0 °C

4.1: BH₃*Me₂S / CH₂Cl₂ / 1 h / 0 - 20 °C

4.2: 88 percent / BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 0 °C

5.1: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 0.25 h / 20 °C

6.1: mesyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6.2: 85 percent / NaH / methanol; diethyl ether / 1 h / 20 °C

7.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: CF₃COOH / H₂O / 3 h / 20 °C

8.2: 82 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 94 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; dimethylsulfide borane complex; AD-mix-β; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; titanium tetrachloride; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 1.1: hydroxylation / 2.1: Cyclization / 3.1: Reduction / 4.1: Ring cleavage / 4.2: Ring cleavage / 5.1: Acylation / 6.1: Substitution / 6.2: Epoxidation / 7.1: Julia coupling / 8.1: Cyclization / 8.2: Elimination / 9.1: debenzylation;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 220384-87-2
{(4S,5R)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2-phenyl-[1,3]dioxolan-4-yl}-methanol

: 252273-45-3
(-)-8-epi-9-deoxygoniopypyrone

Guidance literature:: Multi-step reaction with 6 steps

1.1: BH₃*Me₂S / CH₂Cl₂ / 1 h / 0 - 20 °C

1.2: 88 percent / BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 0 °C

2.1: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 0.25 h / 20 °C

3.1: mesyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 85 percent / NaH / methanol; diethyl ether / 1 h / 20 °C

4.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: CF₃COOH / H₂O / 3 h / 20 °C

5.2: 82 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 94 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; n-butyllithium; dimethylsulfide borane complex; boron trifluoride diethyl etherate; titanium tetrachloride; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; water; 1.1: Ring cleavage / 1.2: Ring cleavage / 2.1: Acylation / 3.1: Substitution / 3.2: Epoxidation / 4.1: Julia coupling / 5.1: Cyclization / 5.2: Elimination / 6.1: debenzylation;
DOI:10.1016/S0040-4020(99)00794-2