(1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione

Base Information

Chemical Name:(1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione
CAS No.:223786-84-3
Molecular Formula:C₁₆H₁₈O₅
Molecular Weight:290.316
Hs Code.:

Synonyms:(1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione

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Chemical Property of (1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione

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Technology Process of (1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione

There total 9 articles about (1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-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: 100.0%

: 223786-83-2
(1R,4R,5R,6S)-4-Hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one

: 223786-84-3
(1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 23 ℃; for 18h;
DOI:10.1016/S0040-4039(99)00040-4

Reference yield:

: 120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7
(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

: 223786-84-3
(1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

2: 91 percent / mCPBA / CH₂Cl₂ / 1.5 h / -10 - 23 °C

3: 99 percent / Dess-Martin reagent / CH₂Cl₂ / 17 h / 23 °C

4: 98 percent / SmI₂ / tetrahydrofuran; methanol / 0.67 h / -78 °C

5: 92 percent / NaH,; TBAI / dimethylformamide / 2.5 h / 23 °C

6: 95 percent / MMPP / aq. ethanol / 2 h / 23 °C

7: 86 percent / KHMDS,; MoOPD / tetrahydrofuran / 7.5 h / -78 °C

8: 100 percent / Dess-Martin reagent / CH₂Cl₂ / 18 h / 23 °C

With lithium aluminium tetrahydride; samarium diiodide; MoOPD; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Cyclization / 3: Oxidation / 4: Reduction / 5: Alkylation / 6: Oxidation / 7: Oxidation / 8: Oxidation;
DOI:10.1016/S0040-4039(99)00040-4

Reference yield:

: 95-12-5,13360-81-1,15507-06-9,42070-72-4,67505-46-8,67671-05-0,67671-06-1,69831-10-3,42070-82-6
(-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol

: 223786-84-3
(1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / mCPBA / CH₂Cl₂ / 1.5 h / -10 - 23 °C

2: 99 percent / Dess-Martin reagent / CH₂Cl₂ / 17 h / 23 °C

3: 98 percent / SmI₂ / tetrahydrofuran; methanol / 0.67 h / -78 °C

4: 92 percent / NaH,; TBAI / dimethylformamide / 2.5 h / 23 °C

5: 95 percent / MMPP / aq. ethanol / 2 h / 23 °C

6: 86 percent / KHMDS,; MoOPD / tetrahydrofuran / 7.5 h / -78 °C

7: 100 percent / Dess-Martin reagent / CH₂Cl₂ / 18 h / 23 °C

With samarium diiodide; MoOPD; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Cyclization / 2: Oxidation / 3: Reduction / 4: Alkylation / 5: Oxidation / 6: Oxidation / 7: Oxidation;
DOI:10.1016/S0040-4039(99)00040-4