Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester
• CAS No.: 315203-91-9
• Molecular Formula: C₃₅H₄₆O₉S
• Molecular Weight: 642.811

Synonyms:Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Chemical Property of Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

There total 28 articles about Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-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:

(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) → Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester (315203-91-9)

Guidance literature:

Multi-step reaction with 23 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; phosphate buffer; tetrapropylammonium perruthennate; borane-THF; pyridine-SO₃ complex; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; 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; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dimeric 9-borabicyclo[3.3.1]nonane; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 2.1: Sharpless asymmetric epoxidation / 4.1: Wittig methylenation / 16.1: Suzuki coupling;

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-en-1-ol (315204-07-0) → Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester (315203-91-9)

Guidance literature:

Multi-step reaction with 22 steps

1.1: 87 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 - 20 °C

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

3.1: 5.38 g / tetrahydrofuran / 0.5 h / 0 °C

4.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

5.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3.5 h / 20 °C

6.1: 97 percent / sodium hydride; tetra-n-butylammonium iodide / dimethylformamide; various solvent(s) / 1.67 h / 20 °C

7.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 1.75 h / 20 °C

7.2: 95 percent / sodium hydroxide; hydrogen peroxide / H₂O / 20 °C

8.1: 76 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1 h / Heating

9.1: 90 percent / p-toluenesulfonic acid monohydrate / methanol; CH₂Cl₂ / 3 h / 20 °C

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

11.1: 3.11 g / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.33 h / 0 °C

12.1: 95 percent / imidazole; triphenylphosphine; iodine / benzene / 0.42 h / 20 °C

13.1: 96 percent / potassium t-butoxide / tetrahydrofuran / 3 h / 0 °C

14.1: tetrahydrofuran / 3 h / 20 °C

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

15.2: 419.6 mg / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / 20 °C

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

16.2: 77 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 - 40 °C

17.1: 88 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

18.1: 261 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

19.1: 94 percent / molecular sieves 4A; tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 1.17 h / 20 °C

20.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; phosphate buffer / CH₂Cl₂; H₂O / 0.67 h / 20 °C / pH 7.0

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

22.1: 723.1 mg / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; phosphate buffer; tetrapropylammonium perruthennate; borane-THF; pyridine-SO₃ complex; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; (-)-diethyl tartrate; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dimeric 9-borabicyclo[3.3.1]nonane; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Sharpless asymmetric epoxidation / 3.1: Wittig methylenation / 15.1: Suzuki coupling;

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) → Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester (315203-91-9)

Guidance literature:

Multi-step reaction with 17 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

With 1H-imidazole; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; phosphate buffer; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 10.1: Suzuki coupling;

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:

Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethanesulfonyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

(4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalene

Acetic acid (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

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