{(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde

Base Information

• Chemical Name: {(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde
• CAS No.: 143521-72-6
• Molecular Formula: C₂₆H₃₄O₄Si
• Molecular Weight: 438.639

Synonyms:{(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde

Chemical Property of {(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde

There total 12 articles about {(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde 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: 96.0%

(4R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-(2-hydroxy-ethyl)-tetrahydro-pyran-2-one (312326-55-9) → {(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde (143521-72-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1016/S0040-4039(00)01337-X

Reference yield:

2-(2-(2-hydroxyethyl)-1,3-dioxolan-2-yl)ethanol (5694-95-1) → {(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde (143521-72-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran

1.2: 76 percent / Bu₄NI

2.1: 97 percent / Dess-Martin periodinane

3.1: 83 percent / Bu₂BOTf / CH₂Cl₂

4.1: 85 percent / LiBH₄ / tetrahydrofuran

5.1: 99 percent / imidazole / dimethylformamide

6.1: 84 percent / EDC / CH₂Cl₂

7.1: 99 percent / FeCl₃; SiO₂ / CHCl₃

8.1: 91 percent / NaH / tetrahydrofuran / 0 °C

9.1: 98 percent / H₂ / Pd(OH)2-C / ethyl acetate

10.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂

With 1H-imidazole; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; silica gel; iron(III) chloride; sodium hydride; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; 1.1: Metallation / 2.1: Oxidation / 3.1: Metallation / 4.1: Reduction / 5.1: Substitution / 6.1: Acylation / 7.1: Ring cleavage / 8.1: Cyclization / 9.1: Catalytic hydrogenation / 10.1: Oxidation;

DOI:10.1016/S0040-4039(00)01337-X

Reference yield:

dimethyl acetonedicarboxylate ethylene ketal (6506-31-6) → {(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde (143521-72-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 99 percent / LiAlH₄ / tetrahydrofuran

2.1: NaH / tetrahydrofuran

2.2: 76 percent / Bu₄NI

3.1: 97 percent / Dess-Martin periodinane

4.1: 83 percent / Bu₂BOTf / CH₂Cl₂

5.1: 85 percent / LiBH₄ / tetrahydrofuran

6.1: 99 percent / imidazole / dimethylformamide

7.1: 84 percent / EDC / CH₂Cl₂

8.1: 99 percent / FeCl₃; SiO₂ / CHCl₃

9.1: 91 percent / NaH / tetrahydrofuran / 0 °C

10.1: 98 percent / H₂ / Pd(OH)2-C / ethyl acetate

11.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂

With 1H-imidazole; lithium aluminium tetrahydride; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; silica gel; iron(III) chloride; sodium hydride; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Metallation / 3.1: Oxidation / 4.1: Metallation / 5.1: Reduction / 6.1: Substitution / 7.1: Acylation / 8.1: Ring cleavage / 9.1: Cyclization / 10.1: Catalytic hydrogenation / 11.1: Oxidation;

DOI:10.1016/S0040-4039(00)01337-X

upstream raw materials:

(4R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-(2-hydroxy-ethyl)-tetrahydro-pyran-2-one

2-(2-(2-hydroxyethyl)-1,3-dioxolan-2-yl)ethanol

dimethyl acetonedicarboxylate ethylene ketal

3-oxopentanedioic acid dimethyl ester

Downstream raw materials:

(E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

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