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

Base Information

• Chemical Name: (1R,4S,5R,6S)-4-Allyl-4-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one
• CAS No.: 223786-85-4
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.397

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

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

Chemical Property:

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

There total 10 articles about (1R,4S,5R,6S)-4-Allyl-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: 98.0%

allyltributylstanane (24850-33-7) + (1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione (223786-84-3) → (1R,4S,5R,6S)-4-Allyl-4-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one (223786-85-4)

Guidance literature:

With lithium perchlorate; In diethyl ether; at 23 ℃; for 22h;

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

Reference yield:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (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) → (1R,4S,5R,6S)-4-Allyl-4-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one (223786-85-4)

Guidance literature:

Multi-step reaction with 9 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

9: 98 percent / LiClO₄ / diethyl ether / 22 h / 23 °C

With lithium aluminium tetrahydride; samarium diiodide; MoOPD; lithium perchlorate; 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 / 9: Alkylation;

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

Reference yield:

(-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol (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) → (1R,4S,5R,6S)-4-Allyl-4-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one (223786-85-4)

Guidance literature:

Multi-step reaction with 8 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

8: 98 percent / LiClO₄ / diethyl ether / 22 h / 23 °C

With samarium diiodide; MoOPD; lithium perchlorate; 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: Cyclization / 2: Oxidation / 3: Reduction / 4: Alkylation / 5: Oxidation / 6: Oxidation / 7: Oxidation / 8: Alkylation;

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

upstream raw materials:

allyltributylstanane

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

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol

Downstream raw materials:

(1R,2S,4S,6R,8S,9R,10S)-2-(Diethyl-isopropyl-silanyloxy)-4-methoxy-9-phenylselanyl-5,7-dioxa-tricyclo[6.2.1.0^2,6]undecane-10-carboxylic acid methyl ester

Diethyl-isopropyl-[(1R,2S,4S,6R,8R,10S)-4-methoxy-10-(4-methoxy-benzyloxymethyl)-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-2-yloxy]-silane

(1R,2S,6R,8R,10S)-2-(Diethyl-isopropyl-silanyloxy)-10-(4-methoxy-benzyloxymethyl)-5,7-dioxa-tricyclo[6.2.1.0^2,6]undecan-4-ol

(1R,4S,5R,6S)-4-Allyl-4-(diethyl-isopropyl-silanyloxy)-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-ol

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