benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester

Base Information

• Chemical Name: benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester
• CAS No.: 1026479-97-9
• Molecular Formula: C₄₇H₆₈O₈Si₃
• Molecular Weight: 845.309
• Mol file: 1026479-97-9.mol

Synonyms:benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester

Chemical Property of benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester

There total 19 articles about benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl 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:

2-propyl 3,4-dideoxy-α-D-erythro-hex-3-enopyranoside (115352-42-6) → benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester (1026479-97-9)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 77 percent / Et₃N / dimethylformamide / 18 h / 20 °C

2.1: 93 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 0.67 h / 20 °C

3.1: pyridine; iodine / CH₂Cl₂ / 1.5 h / 0 °C

4.1: 89.95 g / CeCl₃*7H₂O; NaBH₄ / methanol / 0.08 h / 0 °C

5.1: 100 percent / Pd(OAc)2; CuI; PPh₃ / Et₃N / benzene / 0.5 h / 20 °C

6.1: 20.07 g / PPTS / tetrahydrofuran / 16 h / 20 °C

7.1: 93 percent / K₂CO₃ / 1,2-dichloro-benzene / 5 h / 150 °C

8.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9.1: Pd(OAc)4; KHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

9.2: nBu₄NF / tetrahydrofuran; H₂O / 0.17 h / 20 °C

10.1: 25.47 g / aq. Et₃N / methanol / 15 h / 20 °C

11.1: Et₃N; SO₃*Py / dimethylsulfoxide / 0.33 h / 15 °C

12.1: i-Pr₂NEt / CH₂Cl₂ / 0.33 h / 20 °C

13.1: 22.64 g / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / -78 °C

14.1: MCPBA; K₂CO₃ / CH₂Cl₂ / 0.67 h / 20 °C

14.2: 77 percent / Amberlyst(R) 15 / tetrahydrofuran; H₂O / 0.08 h / 20 °C

15.1: 86 percent / imidazole / dimethylformamide / 10 h / 20 °C

16.1: 94 percent / DMAP / pyridine / 12 h / 20 °C

17.1: H₂SO₄ / methanol / 1 h / 20 °C

17.2: 82 percent / HgO / methanol / 1 h / 20 °C

18.1: Et₃N; 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

19.1: imidazole / dimethylformamide / 10 h / 20 °C

With palladium(II) acetate; pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; palladium diacetate; sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride; pyridine-SO₃ complex; sulfuric acid; iodine; pyridinium p-toluenesulfonate; potassium carbonate; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1,2-dichloro-benzene; benzene; 2.1: Parikh-Doering oxidation / 4.1: Luche's reduction / 5.1: Sonogashira coupling / 7.1: Claisen rearrangement / 11.1: Parikh-Doering oxidation / 13.1: Luche's reduction;

DOI:10.1021/ja0342998

Reference yield:

2-propyl 6-O-tert-butyldimethylsilyl-3,4-dideoxy-α-D-erythro-hex-3-enopyranoside (167628-05-9) → benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester (1026479-97-9)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 93 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 0.67 h / 20 °C

2.1: pyridine; iodine / CH₂Cl₂ / 1.5 h / 0 °C

3.1: 89.95 g / CeCl₃*7H₂O; NaBH₄ / methanol / 0.08 h / 0 °C

4.1: 100 percent / Pd(OAc)2; CuI; PPh₃ / Et₃N / benzene / 0.5 h / 20 °C

5.1: 20.07 g / PPTS / tetrahydrofuran / 16 h / 20 °C

6.1: 93 percent / K₂CO₃ / 1,2-dichloro-benzene / 5 h / 150 °C

7.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8.1: Pd(OAc)4; KHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

8.2: nBu₄NF / tetrahydrofuran; H₂O / 0.17 h / 20 °C

9.1: 25.47 g / aq. Et₃N / methanol / 15 h / 20 °C

10.1: Et₃N; SO₃*Py / dimethylsulfoxide / 0.33 h / 15 °C

11.1: i-Pr₂NEt / CH₂Cl₂ / 0.33 h / 20 °C

12.1: 22.64 g / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / -78 °C

13.1: MCPBA; K₂CO₃ / CH₂Cl₂ / 0.67 h / 20 °C

13.2: 77 percent / Amberlyst(R) 15 / tetrahydrofuran; H₂O / 0.08 h / 20 °C

14.1: 86 percent / imidazole / dimethylformamide / 10 h / 20 °C

15.1: 94 percent / DMAP / pyridine / 12 h / 20 °C

16.1: H₂SO₄ / methanol / 1 h / 20 °C

16.2: 82 percent / HgO / methanol / 1 h / 20 °C

17.1: Et₃N; 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

18.1: imidazole / dimethylformamide / 10 h / 20 °C

With palladium(II) acetate; pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; palladium diacetate; sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride; pyridine-SO₃ complex; sulfuric acid; iodine; pyridinium p-toluenesulfonate; potassium carbonate; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1,2-dichloro-benzene; benzene; 1.1: Parikh-Doering oxidation / 3.1: Luche's reduction / 4.1: Sonogashira coupling / 6.1: Claisen rearrangement / 10.1: Parikh-Doering oxidation / 12.1: Luche's reduction;

DOI:10.1021/ja0342998

Reference yield:

(2S,6S)-6-((tert-butyldimethylsilyloxy)methyl)-2-isopropoxy-2H-pyran-3(6H)-one (588693-26-9) → benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester (1026479-97-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: pyridine; iodine / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 89.95 g / CeCl₃*7H₂O; NaBH₄ / methanol / 0.08 h / 0 °C

3.1: 100 percent / Pd(OAc)2; CuI; PPh₃ / Et₃N / benzene / 0.5 h / 20 °C

4.1: 20.07 g / PPTS / tetrahydrofuran / 16 h / 20 °C

5.1: 93 percent / K₂CO₃ / 1,2-dichloro-benzene / 5 h / 150 °C

6.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7.1: Pd(OAc)4; KHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

7.2: nBu₄NF / tetrahydrofuran; H₂O / 0.17 h / 20 °C

8.1: 25.47 g / aq. Et₃N / methanol / 15 h / 20 °C

9.1: Et₃N; SO₃*Py / dimethylsulfoxide / 0.33 h / 15 °C

10.1: i-Pr₂NEt / CH₂Cl₂ / 0.33 h / 20 °C

11.1: 22.64 g / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / -78 °C

12.1: MCPBA; K₂CO₃ / CH₂Cl₂ / 0.67 h / 20 °C

12.2: 77 percent / Amberlyst(R) 15 / tetrahydrofuran; H₂O / 0.08 h / 20 °C

13.1: 86 percent / imidazole / dimethylformamide / 10 h / 20 °C

14.1: 94 percent / DMAP / pyridine / 12 h / 20 °C

15.1: H₂SO₄ / methanol / 1 h / 20 °C

15.2: 82 percent / HgO / methanol / 1 h / 20 °C

16.1: Et₃N; 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

17.1: imidazole / dimethylformamide / 10 h / 20 °C

With palladium(II) acetate; pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; palladium diacetate; sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride; pyridine-SO₃ complex; sulfuric acid; iodine; pyridinium p-toluenesulfonate; potassium carbonate; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1,2-dichloro-benzene; benzene; 2.1: Luche's reduction / 3.1: Sonogashira coupling / 5.1: Claisen rearrangement / 9.1: Parikh-Doering oxidation / 11.1: Luche's reduction;

DOI:10.1021/ja0342998

upstream raw materials:

tert-butyldimethylsilyl chloride

benzoyl chloride

2-propyl 3,4-dideoxy-α-D-erythro-hex-3-enopyranoside

2-propyl 6-O-tert-butyldimethylsilyl-3,4-dideoxy-α-D-erythro-hex-3-enopyranoside

Downstream raw materials:

benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-3-methoxy-5-oxo-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

benzoic acid 5-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester