2-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethanol

Base Information

• Chemical Name: 2-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethanol
• CAS No.: 346584-10-9
• Molecular Formula: C₂₇H₄₀O₇
• Molecular Weight: 476.61

Synonyms:

Chemical Property of 2-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethanol

There total 36 articles about 2-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethanol 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-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethoxy]-triisopropyl-silane → 2-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethanol (346584-10-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.75h;

DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid methyl ester (213815-23-7) → 2-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethanol (346584-10-9)

Guidance literature:

Multi-step reaction with 36 steps

1.1: 7.34 g / DIBALH / CH₂Cl₂; toluene / 2 h / -78 °C

2.1: 87 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 - 20 °C

3.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

4.1: 5.38 g / tetrahydrofuran / 0.5 h / 0 °C

5.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

6.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3.5 h / 20 °C

7.1: 97 percent / sodium hydride; tetra-n-butylammonium iodide / dimethylformamide; various solvent(s) / 1.67 h / 20 °C

8.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 1.75 h / 20 °C

8.2: 95 percent / sodium hydroxide; hydrogen peroxide / H₂O / 20 °C

9.1: 76 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1 h / Heating

10.1: 90 percent / p-toluenesulfonic acid monohydrate / methanol; CH₂Cl₂ / 3 h / 20 °C

11.1: imidazole / dimethylformamide / 9 h / 50 °C

12.1: 3.11 g / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.33 h / 0 °C

13.1: 95 percent / imidazole; triphenylphosphine; iodine / benzene / 0.42 h / 20 °C

14.1: 96 percent / potassium t-butoxide / tetrahydrofuran / 3 h / 0 °C

15.1: tetrahydrofuran / 3 h / 20 °C

16.1: NaHCO₃; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂ / tetrahydrofuran; H₂O; dimethylformamide / 24 h / 20 °C

16.2: 419.6 mg / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / 20 °C

17.1: BH₃*THF / tetrahydrofuran / -30 °C

17.2: 77 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 - 40 °C

18.1: 88 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

19.1: 261 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

20.1: 94 percent / molecular sieves 4A; tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 1.17 h / 20 °C

21.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; phosphate buffer / CH₂Cl₂; H₂O / 0.67 h / 20 °C / pH 7.0

22.1: NaHCO₃; Zn(OTf)2 / CH₂Cl₂ / 20 °C

23.1: 723.1 mg / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

24.1: 96 percent / m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.25 h / 20 °C

25.1: 90 percent / CH₂Cl₂; hexane / 5 h / -78 - 20 °C

26.1: sodium methoxide / methanol; CH₂Cl₂ / 0.58 h / 20 °C

27.1: 35.8 mg / pyridinium p-toluenesulfonate / CH₂Cl₂; dimethylformamide / 20 °C

28.1: hydrogen / Pd(OH)2/C / ethyl acetate / 20 °C

29.1: 185.5 mg / imidazole / CH₂Cl₂ / 22 h / 20 °C

30.1: 99 percent / molecular sieves 4A; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

31.1: 92 percent / tetrahydrofuran / 3.5 h / -78 - 20 °C

32.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O / 36 h / 20 °C

32.2: 96 percent / NaHSO₃; pyridine / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

33.1: 99 percent / 4-(dimethylamino)pyridine / 1,2-dichloro-etha

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; osmium(VIII) oxide; lithium aluminium tetrahydride; phosphate buffer; tetrapropylammonium perruthennate; borane-THF; pyridine-SO₃ complex; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; (-)-diethyl tartrate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dimeric 9-borabicyclo[3.3.1]nonane; palladium dihydroxide; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 2.1: Sharpless asymmetric epoxidation / 4.1: Wittig methylenation / 16.1: Suzuki coupling / 31.1: Wittig methylenation;

DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

(2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (315203-85-1) → 2-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-ethanol (346584-10-9)

Guidance literature:

Multi-step reaction with 30 steps

1.1: 97 percent / sodium hydride; tetra-n-butylammonium iodide / dimethylformamide; various solvent(s) / 1.67 h / 20 °C

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 1.75 h / 20 °C

2.2: 95 percent / sodium hydroxide; hydrogen peroxide / H₂O / 20 °C

3.1: 76 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1 h / Heating

4.1: 90 percent / p-toluenesulfonic acid monohydrate / methanol; CH₂Cl₂ / 3 h / 20 °C

5.1: imidazole / dimethylformamide / 9 h / 50 °C

6.1: 3.11 g / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.33 h / 0 °C

7.1: 95 percent / imidazole; triphenylphosphine; iodine / benzene / 0.42 h / 20 °C

8.1: 96 percent / potassium t-butoxide / tetrahydrofuran / 3 h / 0 °C

9.1: tetrahydrofuran / 3 h / 20 °C

10.1: NaHCO₃; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂ / tetrahydrofuran; H₂O; dimethylformamide / 24 h / 20 °C

10.2: 419.6 mg / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / 20 °C

11.1: BH₃*THF / tetrahydrofuran / -30 °C

11.2: 77 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 - 40 °C

12.1: 88 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

13.1: 261 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

14.1: 94 percent / molecular sieves 4A; tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 1.17 h / 20 °C

15.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; phosphate buffer / CH₂Cl₂; H₂O / 0.67 h / 20 °C / pH 7.0

16.1: NaHCO₃; Zn(OTf)2 / CH₂Cl₂ / 20 °C

17.1: 723.1 mg / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

18.1: 96 percent / m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.25 h / 20 °C

19.1: 90 percent / CH₂Cl₂; hexane / 5 h / -78 - 20 °C

20.1: sodium methoxide / methanol; CH₂Cl₂ / 0.58 h / 20 °C

21.1: 35.8 mg / pyridinium p-toluenesulfonate / CH₂Cl₂; dimethylformamide / 20 °C

22.1: hydrogen / Pd(OH)2/C / ethyl acetate / 20 °C

23.1: 185.5 mg / imidazole / CH₂Cl₂ / 22 h / 20 °C

24.1: 99 percent / molecular sieves 4A; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

25.1: 92 percent / tetrahydrofuran / 3.5 h / -78 - 20 °C

26.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O / 36 h / 20 °C

26.2: 96 percent / NaHSO₃; pyridine / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

27.1: 99 percent / 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 20 °C

28.1: 75 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 0 - 20 °C

29.1: potassium hydride / tetrahydrofuran; various solvent(s) / 0 - 20 °C

30.1: 93.3 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

With 1H-imidazole; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; osmium(VIII) oxide; lithium aluminium tetrahydride; phosphate buffer; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dimeric 9-borabicyclo[3.3.1]nonane; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 10.1: Suzuki coupling / 25.1: Wittig methylenation;

DOI:10.1016/S0040-4020(01)00164-8

upstream raw materials:

(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid methyl ester

(2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine

2-((2R,4aR,6S,7R,8aS)-7-Benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethanol

Downstream raw materials:

(E)-4-((4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-2,2,9,10a-tetramethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl)-but-2-enoic acid benzyl ester

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