Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradec-12-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradec-12-yl ester
• CAS No.: 80878-31-5
• Molecular Formula: C₂₈H₄₂O₇S
• Molecular Weight: 522.703

Synonyms:Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradec-12-yl ester

Chemical Property of Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradec-12-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradec-12-yl ester

There total 14 articles about Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradec-12-yl ester 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) → Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradec-12-yl ester (80878-31-5)

Guidance literature:

Multi-step reaction with 15 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

With pyridine; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; bis(acetylacetonate)oxovanadium; potassium tert-butylate; hydrogen; sodium acetate; 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; 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 → Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradec-12-yl ester (80878-31-5)

Guidance literature:

Multi-step reaction with 12 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

With pyridine; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; bis(acetylacetonate)oxovanadium; potassium tert-butylate; hydrogen; sodium acetate; potassium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; trifluoroacetic acid; zinc; trichlorophosphate; N-bromoacetamide; palladium/alumina; manganese(II) oxide; In tetrahydrofuran; pyridine; methanol; 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) → Methanesulfonic acid (1S,2S,3R,6R,7S,8R,9R,12S,14S)-9-benzyloxy-6-hydroxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.01,8]tetradec-12-yl ester (80878-31-5)

Guidance literature:

Multi-step reaction with 13 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

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

DOI:10.1021/ja00370a067

upstream raw materials:

methanesulfonyl chloride

(1R,2R,3S,6S,7R,8S,9S,12R,14R)-9-Benzyloxy-3-methoxymethoxy-2,7,14-trimethyl-4-methylene-tricyclo[5.4.3.0^1,8]tetradecane-6,12-diol

C₂₅H₃₂O₃

C₂₅H₃₂O₄

Downstream raw materials:

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

(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

(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

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