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

Base Information

Chemical Name:(1R,4R,5R,6S)-4-Hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one
CAS No.:223786-83-2
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

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

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Chemical Property of (1R,4R,5R,6S)-4-Hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one

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Technology Process of (1R,4R,5R,6S)-4-Hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one

There total 8 articles about (1R,4R,5R,6S)-4-Hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-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: 86.0%

: 223786-82-1
(1S,5S,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one

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

Guidance literature:: With MoOPD; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 7.5h;
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

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

Guidance literature:: Multi-step reaction with 7 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

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;
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

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

Guidance literature:: Multi-step reaction with 6 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

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;
DOI:10.1016/S0040-4039(99)00040-4