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

Base Information

• Chemical Name: (1R,4S,5R,6S)-4-Allyl-4-(diethyl-isopropyl-silanyloxy)-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-ol
• CAS No.: 223786-87-6
• Molecular Formula: C₂₆H₄₂O₅Si
• Molecular Weight: 462.702
• Mol file: 223786-87-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (1R,4S,5R,6S)-4-Allyl-4-(diethyl-isopropyl-silanyloxy)-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-ol 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%

(1R,4S,5R,6S)-4-Allyl-4-(diethyl-isopropyl-silanyloxy)-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one (223786-86-5) → (1R,4S,5R,6S)-4-Allyl-4-(diethyl-isopropyl-silanyloxy)-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-ol (223786-87-6)

Guidance literature:

With chloro-trimethyl-silane; diisobutylaluminium hydride; In dichloromethane; at -95 ℃; for 0.5h;

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-(diethyl-isopropyl-silanyloxy)-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-ol (223786-87-6)

Guidance literature:

Multi-step reaction with 11 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

10: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 6.5 h / 23 °C

11: 98 percent / DIBAL-H,; TMSCl / CH₂Cl₂ / 0.5 h / -95 °C

With lithium aluminium tetrahydride; chloro-trimethyl-silane; samarium diiodide; MoOPD; lithium perchlorate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 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 / 10: Alkylation / 11: Reduction;

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-(diethyl-isopropyl-silanyloxy)-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-ol (223786-87-6)

Guidance literature:

Multi-step reaction with 10 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

9: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 6.5 h / 23 °C

10: 98 percent / DIBAL-H,; TMSCl / CH₂Cl₂ / 0.5 h / -95 °C

With chloro-trimethyl-silane; samarium diiodide; MoOPD; lithium perchlorate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 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 / 9: Alkylation / 10: Reduction;

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

upstream raw materials:

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

(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

(1S,4S,5S)-5-Hydroxymethyl-bicyclo[2.2.1]heptan-2-one

Downstream raw materials:

(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,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