1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one

Base Information

Chemical Name:1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one
CAS No.:847835-11-4
Molecular Formula:C₃₁H₄₂O₆Si
Molecular Weight:538.756
Hs Code.:

Synonyms:1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one

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Chemical Property of 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one

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Technology Process of 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one

There total 12 articles about 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one 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:

: 136787-40-1
(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)acetaldehyde

: 847835-11-4
1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: p-TsOH / benzene / Heating

2: K₂CO₃ / methanol

3: imidazole / dimethylformamide / 10 °C

4: NaH / dimethylformamide

5: 75 percent / TBAF / tetrahydrofuran

6: 2,6-di-t-butylpyridine / CH₂Cl₂ / -50 °C

7: 80 percent / HMPA / tetrahydrofuran / -78 °C

8: Cs₂CO₃ / methanol

9: 70 percent / AgNO₃; NIS / acetone

10: NiCl₂; CrCl₂ / tetrahydrofuran

11: 80 percent / TPAP; NMO / CH₂Cl₂

12: 65 percent / [(Ph₃P)CuH]6 / toluene; H₂O

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-iodo-succinimide; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; (triphenylphosphine)copper(I) hydride hexamer; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; silver nitrate; chromium dichloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene; 12: double Stryker-type reduction;
DOI:10.1016/j.tetlet.2004.12.056

Reference yield:

: 849361-64-4
acetic acid 3-acetoxy-6-(2,3-dihydroxy-propyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester

: 847835-11-4
1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one

Guidance literature:: Multi-step reaction with 13 steps

1: NaIO₄; aq. NaHCO₃ / CH₂Cl₂

2: p-TsOH / benzene / Heating

3: K₂CO₃ / methanol

4: imidazole / dimethylformamide / 10 °C

5: NaH / dimethylformamide

6: 75 percent / TBAF / tetrahydrofuran

7: 2,6-di-t-butylpyridine / CH₂Cl₂ / -50 °C

8: 80 percent / HMPA / tetrahydrofuran / -78 °C

9: Cs₂CO₃ / methanol

10: 70 percent / AgNO₃; NIS / acetone

11: NiCl₂; CrCl₂ / tetrahydrofuran

12: 80 percent / TPAP; NMO / CH₂Cl₂

13: 65 percent / [(Ph₃P)CuH]6 / toluene; H₂O

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; N-iodo-succinimide; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; (triphenylphosphine)copper(I) hydride hexamer; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; silver nitrate; chromium dichloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene; 13: double Stryker-type reduction;
DOI:10.1016/j.tetlet.2004.12.056

Reference yield:

: 2873-29-2
D-glucal triacetate

: 847835-11-4
1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pentan-2-one

Guidance literature:: Multi-step reaction with 15 steps

1: TFA / acetonitrile / 0 °C

2: K₂OsO₄; NMO / tetrahydrofuran; H₂O

3: NaIO₄; aq. NaHCO₃ / CH₂Cl₂

4: p-TsOH / benzene / Heating

5: K₂CO₃ / methanol

6: imidazole / dimethylformamide / 10 °C

7: NaH / dimethylformamide

8: 75 percent / TBAF / tetrahydrofuran

9: 2,6-di-t-butylpyridine / CH₂Cl₂ / -50 °C

10: 80 percent / HMPA / tetrahydrofuran / -78 °C

11: Cs₂CO₃ / methanol

12: 70 percent / AgNO₃; NIS / acetone

13: NiCl₂; CrCl₂ / tetrahydrofuran

14: 80 percent / TPAP; NMO / CH₂Cl₂

15: 65 percent / [(Ph₃P)CuH]6 / toluene; H₂O

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium osmate(VI); sodium periodate; N-iodo-succinimide; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; (triphenylphosphine)copper(I) hydride hexamer; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; silver nitrate; trifluoroacetic acid; chromium dichloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene; 1: Ferrier reaction / 15: double Stryker-type reduction;
DOI:10.1016/j.tetlet.2004.12.056