(2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Base Information

• Chemical Name: (2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene
• CAS No.: 917896-70-9
• Molecular Formula: C₂₉H₃₀O₆
• Molecular Weight: 474.554
• Mol file: 917896-70-9.mol

Synonyms:(2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Chemical Property of (2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

There total 1 articles about (2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 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:

2-bromomethylnaphthyl bromide (939-26-4) + (2R,4aR,5aS,10aR,11R,11aS)-2-(4-Methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-ol (440320-29-6) → (2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (917896-70-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 13h;

DOI:10.1021/ol062350h

Reference yield:

(2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (917896-70-9) → C40H44O10S

Guidance literature:

Multi-step reaction with 19 steps

1: 1.95 g / TFA / tetrahydrofuran; H₂O / 3 h / 20 °C

2: 95 percent / I₂; imidazole; PPh₃ / tetrahydrofuran / 3 h / 20 °C

3: 98 percent / dimethylsulfoxide / 24 h / 40 °C

4: 88 percent / imidazole / dimethylformamide / 72 h / 40 °C

5: DIBAL / CH₂Cl₂; hexane / 0.67 h / -78 °C

6: 740 mg / NaBH₄ / methanol; CH₂Cl₂ / 1.5 h / 0 °C

7: 99 percent / pyridine; n-Bu₃P / 0.67 h / 20 °C

8: NCS / CCl₄; CH₂Cl₂ / 1 h / 20 °C

9: 78 percent / 2,6-di-tert-butyl-4-methylpyridine; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂; CCl₄ / 5 h / -78 - -30 °C

10: 92 percent / i-Pr₂NEt; AgOTf; molecular sieves 4 Angstroem / benzene / 20 °C

11: LiOH*H₂O / dioxane; H₂O / 24 h / 20 °C

12: 131 mg / n-Bu₃P / dimethylformamide / 20 °C

13: (TMS)3SiH; Et₃B / toluene / 20 °C

14: Me₃Al; molecular sieves 4 Angstroem / CH₂Cl₂; hexane / 1 h / -90 - -55 °C

15: benzene / 3 h / 140 °C

16: 24.1 mg / Pd(OAc)2 / acetonitrile / 1.5 h / 20 °C

17: 88 percent / HF / acetonitrile; H₂O / 1 h / 20 °C

18: 86 percent / Et₃SiH; TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -65 - -30 °C

19: 94 percent / pyridine; molecular sieves 4 Angstroem / 8 h / 20 °C

With pyridine; 1H-imidazole; triethylsilane; lithium hydroxide; sodium tetrahydroborate; N-chloro-succinimide; 2,6-di-tert-butyl-4-methylpyridine; triethyl borane; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; tris-(trimethylsilyl)silane; 4 A molecular sieve; hydrogen fluoride; iodine; trimethylaluminum; silver trifluoromethanesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 16: Saegusa oxidation;

DOI:10.1021/ol062350h

Reference yield:

(2R,4aR,5aS,10aS,11R,11aR)-2-(4-Methoxy-phenyl)-11-(naphthalen-2-ylmethoxy)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (917896-70-9) → 14-[3-(tert-butyl-dimethyl-silanyloxy)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl]-6-(4-methoxy-phenyl)-2,5,7,13-tetraoxa-tricyclo[10.5.0.03,8]heptadeca-9,16-dien-15-one

Guidance literature:

Multi-step reaction with 16 steps

1: 1.95 g / TFA / tetrahydrofuran; H₂O / 3 h / 20 °C

2: 95 percent / I₂; imidazole; PPh₃ / tetrahydrofuran / 3 h / 20 °C

3: 98 percent / dimethylsulfoxide / 24 h / 40 °C

4: 88 percent / imidazole / dimethylformamide / 72 h / 40 °C

5: DIBAL / CH₂Cl₂; hexane / 0.67 h / -78 °C

6: 740 mg / NaBH₄ / methanol; CH₂Cl₂ / 1.5 h / 0 °C

7: 99 percent / pyridine; n-Bu₃P / 0.67 h / 20 °C

8: NCS / CCl₄; CH₂Cl₂ / 1 h / 20 °C

9: 78 percent / 2,6-di-tert-butyl-4-methylpyridine; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂; CCl₄ / 5 h / -78 - -30 °C

10: 92 percent / i-Pr₂NEt; AgOTf; molecular sieves 4 Angstroem / benzene / 20 °C

11: LiOH*H₂O / dioxane; H₂O / 24 h / 20 °C

12: 131 mg / n-Bu₃P / dimethylformamide / 20 °C

13: (TMS)3SiH; Et₃B / toluene / 20 °C

14: Me₃Al; molecular sieves 4 Angstroem / CH₂Cl₂; hexane / 1 h / -90 - -55 °C

15: benzene / 3 h / 140 °C

16: 24.1 mg / Pd(OAc)2 / acetonitrile / 1.5 h / 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; N-chloro-succinimide; 2,6-di-tert-butyl-4-methylpyridine; triethyl borane; tributylphosphine; tris-(trimethylsilyl)silane; 4 A molecular sieve; iodine; trimethylaluminum; silver trifluoromethanesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 16: Saegusa oxidation;

DOI:10.1021/ol062350h

upstream raw materials:

2-bromomethylnaphthyl bromide

(2R,4aR,5aS,10aR,11R,11aS)-2-(4-Methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-ol

Downstream raw materials:

tert-Butyl-dimethyl-[(2R,3R,4R,4aS,9aS)-4-(naphthalen-2-ylmethoxy)-2-(2-phenylsulfanyl-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-silane

tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane