(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

Base Information

• Chemical Name: (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
• CAS No.: 80878-39-3
• Molecular Formula: C₃₁H₄₈O₅
• Molecular Weight: 500.719
• Mol file: 80878-39-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (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

There total 24 articles about (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 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: 50.0%

methyllithium (917-54-4) + 2-[(1S,2S,3R,6S,7S,8S,9R,14S)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,7,14-trimethyl-tricyclo[5.4.3.01,8]tetradec-(4E)-ylidene]-ethanol (80878-38-2) → (1S,2S,3R,4R,6S,7S,8S,9R,14S)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,4,7,14-tetramethyl-4-vinyl-tricyclo[5.4.3.01,8]tetradecane (80878-39-3)

Guidance literature:

With copper(l) iodide; In tetrahydrofuran;

DOI:10.1021/ja00370a067

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,4R,6S,7S,8S,9R,14S)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,4,7,14-tetramethyl-4-vinyl-tricyclo[5.4.3.01,8]tetradecane (80878-39-3)

Guidance literature:

Multi-step reaction with 23 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

19: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / Heating

20: 1.) ozone, 2.) P(OCH₃)3 / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) -78 deg C

21: 2.) 20percent H₂SO₄ / 1.) THF, -35 - -30 deg C, 0.5 h, 2.) aq. THF

22: 95 percent / DIBAH / CH₂Cl₂ / 0 °C

23: 50 percent / CuI, n-Bu₃P+N(CH₃)PhI- / tetrahydrofuran

With pyridine; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; sodium amalgam; copper(l) iodide; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; sulfuric acid; potassium tert-butylate; hydrogen; sodium acetate; sodium; potassium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; zinc; phosphorous acid trimethyl ester; 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:

(3S,3aR,4R,7S,7aS,9R)-3-Benzyloxy-7a-(1-hydroxy-1-methyl-allyl)-7-methoxymethoxy-4,9-dimethyl-octahydro-4,7-ethano-inden-5-one → (1S,2S,3R,4R,6S,7S,8S,9R,14S)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,4,7,14-tetramethyl-4-vinyl-tricyclo[5.4.3.01,8]tetradecane (80878-39-3)

Guidance literature:

Multi-step reaction with 22 steps

1: 79 percent / PCC / CH₂Cl₂

2: 82 percent / tetrahydrofuran / -93 - -80 °C

3: 88 percent / MnO₂ / CH₂Cl₂

4: 61 percent / hydrogen / 10percent Pd/Al₂O₃, MnO / various solvent(s); ethyl acetate / 760 Torr

5: 92 percent / K₂CO₃ / methanol

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

7: 80 percent / CF₃COOH / CH₂Cl₂ / Ambient temperature

8: 97 percent / t-BuOOH, VO(acac)2 / benzene / Ambient temperature

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

10: 71 percent / KH / dimethylformamide; tetrahydrofuran / -30 - -20 °C

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

12: 81 percent / zinc dust, HOAc / methanol / 0.75 h / -20 °C

13: DIBAH / CH₂Cl₂ / 0.17 h / -60 °C

14: pyridine / CH₂Cl₂ / 2 h / 0 °C

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

16: PCC / CH₂Cl₂ / 12 h

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

18: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / Heating

19: 1.) ozone, 2.) P(OCH₃)3 / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) -78 deg C

20: 2.) 20percent H₂SO₄ / 1.) THF, -35 - -30 deg C, 0.5 h, 2.) aq. THF

21: 95 percent / DIBAH / CH₂Cl₂ / 0 °C

22: 50 percent / CuI, n-Bu₃P+N(CH₃)PhI- / tetrahydrofuran

With pyridine; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; sodium amalgam; copper(l) iodide; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; sulfuric acid; potassium tert-butylate; hydrogen; sodium acetate; sodium; potassium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; zinc; phosphorous acid trimethyl ester; 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:

methyllithium

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

C₂₅H₃₂O₃

C₂₅H₃₂O₄

Downstream raw materials:

(+/-)-Mutilin

(+/-)-Pleuromutilin