(1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecan-6-ol

Base Information

• Chemical Name: (1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecan-6-ol
• CAS No.: 80924-96-5
• Molecular Formula: C₂₇H₄₀O₄
• Molecular Weight: 428.612

Synonyms:(1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecan-6-ol

Chemical Property of (1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecan-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecan-6-ol

There total 17 articles about (1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecan-6-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:

(3S,3aS,4R,7S,7aR,9R)-7a-Acetyl-3-benzyloxy-7-methoxymethoxy-4,9-dimethyl-octahydro-4,7-ethano-inden-5-one (80878-24-6) → (1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecan-6-ol (80924-96-5)

Guidance literature:

Multi-step reaction with 18 steps

1: 67 percent / tetrahydrofuran; diethyl ether / -40 °C

2: 79 percent / PCC / CH₂Cl₂

3: 82 percent / tetrahydrofuran / -93 - -80 °C

4: 88 percent / MnO₂ / CH₂Cl₂

5: 61 percent / hydrogen / 10percent Pd/Al₂O₃, MnO / various solvent(s); ethyl acetate / 760 Torr

6: 92 percent / K₂CO₃ / methanol

7: POCl₃, DMAP / CH₂Cl₂; pyridine / 35 °C

8: 80 percent / CF₃COOH / CH₂Cl₂ / Ambient temperature

9: 97 percent / t-BuOOH, VO(acac)2 / benzene / Ambient temperature

10: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -30 °C

11: 71 percent / KH / dimethylformamide; tetrahydrofuran / -30 - -20 °C

12: N-bromoacetamide, NaOAc / methanol; H₂O / 8.5 h / 25 °C

13: 81 percent / zinc dust, HOAc / methanol / 0.75 h / -20 °C

14: DIBAH / CH₂Cl₂ / 0.17 h / -60 °C

15: pyridine / CH₂Cl₂ / 2 h / 0 °C

16: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

17: PCC / CH₂Cl₂ / 12 h

18: Na, 5percent Na/Hg / ethanol / 2 h / 25 °C

With pyridine; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; sodium amalgam; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; potassium tert-butylate; hydrogen; sodium acetate; sodium; potassium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; trifluoroacetic acid; zinc; trichlorophosphate; N-bromoacetamide; palladium/alumina; manganese(II) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/ja00370a067

Reference yield:

(3R,3aS,4S,7R,7aR,9S)-3-Benzyloxy-7a-((E)-3-hydroxy-1-methyl-but-1-enyl)-7-methoxymethoxy-4,9-dimethyl-octahydro-4,7-ethano-inden-5-one → (1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecan-6-ol (80924-96-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 88 percent / MnO₂ / CH₂Cl₂

2: 61 percent / hydrogen / 10percent Pd/Al₂O₃, MnO / various solvent(s); ethyl acetate / 760 Torr

3: 92 percent / K₂CO₃ / methanol

4: POCl₃, DMAP / CH₂Cl₂; pyridine / 35 °C

5: 80 percent / CF₃COOH / CH₂Cl₂ / Ambient temperature

6: 97 percent / t-BuOOH, VO(acac)2 / benzene / Ambient temperature

7: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -30 °C

8: 71 percent / KH / dimethylformamide; tetrahydrofuran / -30 - -20 °C

9: N-bromoacetamide, NaOAc / methanol; H₂O / 8.5 h / 25 °C

10: 81 percent / zinc dust, HOAc / methanol / 0.75 h / -20 °C

11: DIBAH / CH₂Cl₂ / 0.17 h / -60 °C

12: pyridine / CH₂Cl₂ / 2 h / 0 °C

13: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

14: PCC / CH₂Cl₂ / 12 h

15: Na, 5percent Na/Hg / ethanol / 2 h / 25 °C

With pyridine; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; sodium amalgam; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; potassium tert-butylate; hydrogen; sodium acetate; sodium; potassium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; trifluoroacetic acid; zinc; trichlorophosphate; N-bromoacetamide; palladium/alumina; manganese(II) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/ja00370a067

Reference yield:

(E)-3-((1R,3aR,4R,7S,7aS,8S)-1-Benzyloxy-4-methoxymethoxy-7,8-dimethyl-6-oxo-octahydro-4,7-ethano-inden-3a-yl)-but-2-enal (80878-25-7) → (1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradecan-6-ol (80924-96-5)

Guidance literature:

Multi-step reaction with 16 steps

1: 82 percent / tetrahydrofuran / -93 - -80 °C

2: 88 percent / MnO₂ / CH₂Cl₂

3: 61 percent / hydrogen / 10percent Pd/Al₂O₃, MnO / various solvent(s); ethyl acetate / 760 Torr

4: 92 percent / K₂CO₃ / methanol

5: POCl₃, DMAP / CH₂Cl₂; pyridine / 35 °C

6: 80 percent / CF₃COOH / CH₂Cl₂ / Ambient temperature

7: 97 percent / t-BuOOH, VO(acac)2 / benzene / Ambient temperature

8: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -30 °C

9: 71 percent / KH / dimethylformamide; tetrahydrofuran / -30 - -20 °C

10: N-bromoacetamide, NaOAc / methanol; H₂O / 8.5 h / 25 °C

11: 81 percent / zinc dust, HOAc / methanol / 0.75 h / -20 °C

12: DIBAH / CH₂Cl₂ / 0.17 h / -60 °C

13: pyridine / CH₂Cl₂ / 2 h / 0 °C

14: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

15: PCC / CH₂Cl₂ / 12 h

16: Na, 5percent Na/Hg / ethanol / 2 h / 25 °C

With pyridine; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; sodium amalgam; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; potassium tert-butylate; hydrogen; sodium acetate; sodium; potassium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; trifluoroacetic acid; zinc; trichlorophosphate; N-bromoacetamide; palladium/alumina; manganese(II) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/ja00370a067

upstream raw materials:

(1S,2S,3R,7S,8S,9R,14S)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecan-6-one

C₂₅H₃₂O₃

C₂₅H₃₂O₄

(3S,3aS,4R,7S,7aR,9R)-7a-Acetyl-3-benzyloxy-7-methoxymethoxy-4,9-dimethyl-octahydro-4,7-ethano-inden-5-one

Downstream raw materials:

(1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecane

[(1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradec-(4E)-ylidene]-acetaldehyde

2-[(1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradec-(4E)-ylidene]-ethanol

(1S,2S,3R,4R,6S,7S,8S,9R,14S)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,4,7,14-tetramethyl-4-vinyl-tricyclo[5.4.3.0^1,8]tetradecane

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