benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester

Base Information

• Chemical Name: benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester
• CAS No.: 1026979-90-7
• Molecular Formula: C₄₁H₅₄O₈Si₂
• Molecular Weight: 731.046
• Mol file: 1026979-90-7.mol

Synonyms:benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester

Chemical Property of benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester

There total 18 articles about benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-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:

2-propyl 3,4-dideoxy-α-D-erythro-hex-3-enopyranoside (115352-42-6) → benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester (1026979-90-7)

Guidance literature:

Multi-step reaction with 20 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

20.1: n-Bu₄NF / tetrahydrofuran; H₂O / 7 h / 0 °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; tetrabutyl ammonium fluoride; 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; water; 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-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester (1026979-90-7)

Guidance literature:

Multi-step reaction with 19 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

19.1: n-Bu₄NF / tetrahydrofuran; H₂O / 7 h / 0 °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; tetrabutyl ammonium fluoride; 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; water; 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-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester (1026979-90-7)

Guidance literature:

Multi-step reaction with 18 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

18.1: n-Bu₄NF / tetrahydrofuran; H₂O / 7 h / 0 °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; tetrabutyl ammonium fluoride; 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; water; 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:

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

(2S,6S)-6-((tert-butyldimethylsilyloxy)methyl)-2-isopropoxy-2H-pyran-3(6H)-one

6-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-isopropoxy-6H-pyran-3-one

Downstream raw materials:

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

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