(R_S)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone

Base Information

• Chemical Name: (R_S)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone
• CAS No.: 113476-99-6
• Molecular Formula: C₅₀H₆₄O₆SSi₂
• Molecular Weight: 849.292

Synonyms:(R_S)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone

Chemical Property of (R_S)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone

Chemical Property:

Purity/Quality:

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Technology Process of (R_S)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone

There total 11 articles about (R_S)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone 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: 93.0%

7-(tert-Butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(2,2-dimethyl-[1,3]dioxan-5-yl)-2-((R)-toluene-4-sulfinyl)-heptan-3-one → (RS)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone (113476-99-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 50 ℃; for 5h;

DOI:10.1248/cpb.41.339

Reference yield:

diethyl 2-(3-oxo-propyl)malonate (19515-61-8) → (RS)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone (113476-99-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / p-toluenesulfonic monohydrate / benzene / 24 h / Heating

2: 80 percent / LiAlH₄ / diethyl ether / 15 h / Ambient temperature

3: 96 percent / imidazole / dimethylformamide / 4.5 h / Ambient temperature

4: 62 percent / p-toluenesulfonic acid monohydrate / acetone / 8 h / 50 °C

5: 1.) LDA / 1.) n-hexane, THF, -29 deg C, 30 min, 2.) n-hexane, THF, -78 drg C, 2 h

6: 87 percent / AcONa, PCC / CH₂Cl₂ / 12 h / Ambient temperature

7: 32 percent / K₂CO₃, 18-crown-6 / acetonitrile / 12 h / 35 °C

8: 93 percent / 0.05N HCl / tetrahydrofuran / 5 h / 50 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; 18-crown-6 ether; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1248/cpb.41.339

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (RS)-1,1-bis(tert-butyldiphenylsilyloxymethyl)-7,7-bis(hydroxymethyl)-5-(p-tolyl)sulfinyl-4-heptanone (113476-99-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) n-hexane, THF, -29 deg C, 30 min, 2.) n-hexane, THF, -78 drg C, 2 h

2: 87 percent / AcONa, PCC / CH₂Cl₂ / 12 h / Ambient temperature

3: 32 percent / K₂CO₃, 18-crown-6 / acetonitrile / 12 h / 35 °C

4: 93 percent / 0.05N HCl / tetrahydrofuran / 5 h / 50 °C

With hydrogenchloride; 18-crown-6 ether; sodium acetate; potassium carbonate; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1248/cpb.41.339

upstream raw materials:

5-iodomethyl-2,2-dimethyl-1,3-dioxane

(R_S)-5,5-bis(tert-butyldiphenylsilyloxymethyl)-1-(p-tolyl)sulfinyl-2-pentanone

Ethyl 2-ethoxycarbonyl-4-(1',3'-dioxolan-2'-yl)butanoate

diethyl 2-(3-oxo-propyl)malonate

Downstream raw materials:

1-[4-(tert-Butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-butyl]-7-((S)-toluene-4-sulfinyl)-2,6-dioxa-bicyclo[2.2.2]octane

(3S,5S,6R,9R,R_S)-3-benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfinyl-1,7-dioxaspiro<5.5>undecane

[(3S,6R,9S,11S)-9-Benzyloxymethyl-11-((R)-toluene-4-sulfinyl)-1,7-dioxa-spiro[5.5]undec-3-yl]-methanol

Trifluoro-acetic acid (3S,4R,6S,9S)-3-benzyloxymethyl-9-ethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

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