(2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone

Base Information

• Chemical Name: (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone
• CAS No.: 331627-44-2
• Molecular Formula: C₂₈H₃₈O₅
• Molecular Weight: 454.607
• Mol file: 331627-44-2.mol

Synonyms:(2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone

Chemical Property of (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone

There total 14 articles about (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone 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: 92.0%

2-tetrahydropyranyloxy-1-iodoethane (96388-83-9) + (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-[1,8-bc]-3,6-dimethylnaphtho-2-furanone (331627-42-0) → (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone (331627-44-2)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 0 ℃; for 2h;

DOI:10.1021/jo0015772

Reference yield:

(S)-6-hydroxymethyl-3-(methoxymethoxy)-6-methyl-2-cyclohexenone (252979-17-2) → (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone (331627-44-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / imidazole / dimethylformamide / 10 h / 20 °C

2: 21.6 g / tetrahydrofuran / 6 h / 0 °C

3: 93 percent / Et₃N / benzene / 1 h / 20 °C

4: 8.75 g / DIBAL-H / toluene / 0.5 h / -78 °C

5: 97 percent / m-CPBA; Na₂HPO₄ / CHCl₃ / 0.5 h / -42 °C

6: 98 percent / DEAD; PPh₃ / tetrahydrofuran / 1 h / 20 °C

7: 89 percent / ethyl propiolate / pyridine; toluene / 8 h / Heating

8: 88 percent / CuI / diethyl ether / 0.25 h / 0 °C

9: 100 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

10: 93 percent / NaH; n-Bu₄NI / dimethylformamide; tetrahydrofuran / 24 h / 20 °C

11: 92 percent / LDA / tetrahydrofuran; hexane / 2 h / 0 °C

With 1H-imidazole; disodium hydrogenphosphate; copper(l) iodide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; propynoic acid ethyl ester; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; pyridine; diethyl ether; hexane; chloroform; N,N-dimethyl-formamide; toluene; benzene; 6: Mitsunobu reaction / 7: intramolecular Diels-Alder reaction;

DOI:10.1021/jo0015772

Reference yield:

(R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-vinyl-2-cyclohexenone (331627-25-9) → (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-[2-(tetrahydro-2-pyranyloxy)ethyl]-[1,8-bc]-naphtho-2-furanone (331627-44-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / Et₃N / benzene / 1 h / 20 °C

2: 8.75 g / DIBAL-H / toluene / 0.5 h / -78 °C

3: 97 percent / m-CPBA; Na₂HPO₄ / CHCl₃ / 0.5 h / -42 °C

4: 98 percent / DEAD; PPh₃ / tetrahydrofuran / 1 h / 20 °C

5: 89 percent / ethyl propiolate / pyridine; toluene / 8 h / Heating

6: 88 percent / CuI / diethyl ether / 0.25 h / 0 °C

7: 100 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

8: 93 percent / NaH; n-Bu₄NI / dimethylformamide; tetrahydrofuran / 24 h / 20 °C

9: 92 percent / LDA / tetrahydrofuran; hexane / 2 h / 0 °C

With disodium hydrogenphosphate; copper(l) iodide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; propynoic acid ethyl ester; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; pyridine; diethyl ether; hexane; chloroform; N,N-dimethyl-formamide; toluene; benzene; 4: Mitsunobu reaction / 5: intramolecular Diels-Alder reaction;

DOI:10.1021/jo0015772

upstream raw materials:

2-tetrahydropyranyloxy-1-iodoethane

(2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-[1,8-bc]-3,6-dimethylnaphtho-2-furanone

benzyl bromide

(S)-6-hydroxymethyl-3-(methoxymethoxy)-6-methyl-2-cyclohexenone