(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-one

Base Information

• Chemical Name: (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-one
• CAS No.: 221373-04-2
• Molecular Formula: C₂₂H₂₈O₄Si
• Molecular Weight: 384.547

Synonyms:(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-one

Chemical Property of (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-one

Chemical Property:

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Technology Process of (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-one

There total 5 articles about (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-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: 80.0%

(1S,4R,6S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3,7-dioxa-bicyclo[4.1.0]heptan-5-one (221373-02-0) → (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-one (221373-04-2)

Guidance literature:

With sodium acetate; acetic acid; sodium iodide; In acetone; at 25 ℃; for 0.166667h;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

Reference yield:

(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (125901-90-8) → (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-one (221373-04-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / imidazole / dimethylformamide / 1 h / 0 °C

2: 75 percent / m-CPBA / CH₂Cl₂ / 12 h / 25 °C

3: 86 percent / PDC, 3 Angstroem molecular sieves / CH₂Cl₂ / 6 h / 25 °C

4: 80 percent / NaI, NaOAc, AcOH / acetone / 0.17 h / 25 °C

With 1H-imidazole; dipyridinium dichromate; 3 A molecular sieve; sodium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-dihydro-pyran-3-one (221373-04-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / imidazole / dimethylformamide / 1 h / 0 °C

2: 75 percent / m-CPBA / CH₂Cl₂ / 12 h / 25 °C

3: 86 percent / PDC, 3 Angstroem molecular sieves / CH₂Cl₂ / 6 h / 25 °C

4: 80 percent / NaI, NaOAc, AcOH / acetone / 0.17 h / 25 °C

With 1H-imidazole; dipyridinium dichromate; 3 A molecular sieve; sodium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

upstream raw materials:

(1S,4R,6S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3,7-dioxa-bicyclo[4.1.0]heptan-5-one

(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

tert-butylchlorodiphenylsilane

2-(tert-butyl-diphenyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

Downstream raw materials:

2,2-Dimethyl-propionic acid (3R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5,5-bis-ethylsulfanyl-tetrahydro-pyran-3-yl ester

2,2-Dimethyl-propionic acid (3R,6R)-5,5-bis-ethylsulfanyl-6-[(Z)-3-((2R,4S,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-propenyl]-tetrahydro-pyran-3-yl ester

2,2-Dimethyl-propionic acid (3R,6R)-6-{(Z)-3-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-propenyl}-5,5-bis-ethylsulfanyl-tetrahydro-pyran-3-yl ester

(3R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5,5-bis-ethylsulfanyl-tetrahydro-pyran-3-ol

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