(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

Base Information

Chemical Name:(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
CAS No.:346584-11-0
Molecular Formula:C₃₆H₄₆O₈
Molecular Weight:606.756
Hs Code.:

(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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Suppliers and Price of (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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Chemical Property of (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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Technology Process of (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

There total 38 articles about (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 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:

: 213815-23-7
(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid methyl ester

: 346584-11-0
(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

Guidance literature:: Multi-step reaction with 38 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 / 38.1: Wittig homologation;
DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

: 315203-98-6
2-((2R,4aR,6S,7R,8aS)-7-Benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethanol

: 346584-11-0
(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

Guidance literature:: Multi-step reaction with 30 steps

1.1: 76 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1 h / Heating

2.1: 90 percent / p-toluenesulfonic acid monohydrate / methanol; CH₂Cl₂ / 3 h / 20 °C

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

4.1: 3.11 g / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.33 h / 0 °C

5.1: 95 percent / imidazole; triphenylphosphine; iodine / benzene / 0.42 h / 20 °C

6.1: 96 percent / potassium t-butoxide / tetrahydrofuran / 3 h / 0 °C

7.1: tetrahydrofuran / 3 h / 20 °C

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

8.2: 419.6 mg / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / 20 °C

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

9.2: 77 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 - 40 °C

10.1: 88 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

11.1: 261 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

12.1: 94 percent / molecular sieves 4A; tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 1.17 h / 20 °C

13.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; phosphate buffer / CH₂Cl₂; H₂O / 0.67 h / 20 °C / pH 7.0

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

15.1: 723.1 mg / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

16.1: 96 percent / m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.25 h / 20 °C

17.1: 90 percent / CH₂Cl₂; hexane / 5 h / -78 - 20 °C

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

19.1: 35.8 mg / pyridinium p-toluenesulfonate / CH₂Cl₂; dimethylformamide / 20 °C

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

21.1: 185.5 mg / imidazole / CH₂Cl₂ / 22 h / 20 °C

22.1: 99 percent / molecular sieves 4A; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

23.1: 92 percent / tetrahydrofuran / 3.5 h / -78 - 20 °C

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

24.2: 96 percent / NaHSO₃; pyridine / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

25.1: 99 percent / 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 20 °C

26.1: 75 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 0 - 20 °C

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

28.1: 93.3 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

29.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 1.5 h / 0 °C

30.1: 89.2 mg / 1,2-dichloro-ethane / 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; 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 hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 8.1: Suzuki coupling / 23.1: Wittig methylenation / 30.1: Wittig homologation;
DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

: 315203-85-1
(2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 346584-11-0
(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

Guidance literature:: Multi-step reaction with 32 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

31.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 1.5 h / 0 °C

32.1: 89.2 mg / 1,2-dichloro-ethane / 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; 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; 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; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 10.1: Suzuki coupling / 25.1: Wittig methylenation / 32.1: Wittig homologation;
DOI:10.1016/S0040-4020(01)00164-8