(S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol

Base Information

• Chemical Name: (S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol
• CAS No.: 90941-85-8
• Molecular Formula: C₂₁H₃₆O₅SSi
• Molecular Weight: 428.665
• Mol file: 90941-85-8.mol

Synonyms:(S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol

Chemical Property of (S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol

There total 19 articles about (S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol 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: 87.0%

(S)-1-[(4R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-phenylsulfanyl-ethanol → (S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol (90941-85-8)

Guidance literature:

With sodium periodate; In methanol; water; at 0 ℃;

DOI:10.1021/jo00189a046

Reference yield:

(E)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol (90941-89-2) → (S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol (90941-85-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 77 percent / Ti(O-i-Pr)4, diethyl (-)-tartrate, TBHP / CH₂Cl₂ / -20 °C

2: 90 percent / pyridine / tetrahydrofuran / -20 deg C -> rt

3: 1) AlCl₃, 2) 1percent aq. H₂SO₄ / 1) Et₂O, -20 deg C, 2) CH₃OH, rt

4: 74 percent / imidazole / tetrahydrofuran / -20 °C

5: 92 percent / p-TsOH / acetone / Ambient temperature

6: 100 percent / K₂CO₃ / methanol / Ambient temperature

7: 77 percent / Et₃N / acetonitrile / -10 °C

8: 1) MsCl, Et₃N, 2) n-Bu₄NOH / 1) Et₂O, 0 deg C, 2) Et₂O, MeOH (trace), rt

9: 91 percent / aq. 0.5 N NaOH / tetrahydrofuran / 0 deg C -> rt

10: 87 percent / NaIO₄ / methanol; H₂O / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium periodate; aluminium trichloride; diethyl (2S,3S)-tartrate; sulfuric acid; tetra(n-butyl)ammonium hydroxide; potassium carbonate; methanesulfonyl chloride; triethylamine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jo00189a046

Reference yield:

[(2R,3R)-3-((S)-2,2-Diethyl-[1,3]dioxolan-4-ylmethyl)-oxiranyl]-methanol (90941-90-5) → (S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol (90941-85-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / pyridine / tetrahydrofuran / -20 deg C -> rt

2: 1) AlCl₃, 2) 1percent aq. H₂SO₄ / 1) Et₂O, -20 deg C, 2) CH₃OH, rt

3: 74 percent / imidazole / tetrahydrofuran / -20 °C

4: 92 percent / p-TsOH / acetone / Ambient temperature

5: 100 percent / K₂CO₃ / methanol / Ambient temperature

6: 77 percent / Et₃N / acetonitrile / -10 °C

7: 1) MsCl, Et₃N, 2) n-Bu₄NOH / 1) Et₂O, 0 deg C, 2) Et₂O, MeOH (trace), rt

8: 91 percent / aq. 0.5 N NaOH / tetrahydrofuran / 0 deg C -> rt

9: 87 percent / NaIO₄ / methanol; H₂O / 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium periodate; aluminium trichloride; sulfuric acid; tetra(n-butyl)ammonium hydroxide; potassium carbonate; methanesulfonyl chloride; triethylamine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; acetone; acetonitrile;

DOI:10.1021/jo00189a046

upstream raw materials:

(E)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

[(2R,3R)-3-((S)-2,2-Diethyl-[1,3]dioxolan-4-ylmethyl)-oxiranyl]-methanol

tert-Butyl-((4S,6R)-2,2-dimethyl-6-(R)-oxiranyl-[1,3]dioxan-4-ylmethoxy)-dimethyl-silane

(S)-4-((1R,3S)-1,3,4-Trihydroxy-butyl)-[1,3]dioxolan-2-one

Downstream raw materials:

(S)-2-Benzenesulfinyl-3-[(4S,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol

(R)-3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol