(4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid

Base Information

Chemical Name:(4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid
CAS No.:115495-43-7
Molecular Formula:C₁₇H₂₄O₅S
Molecular Weight:340.441
Hs Code.:

Synonyms:(4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid

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Chemical Property of (4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid

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Technology Process of (4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid

There total 18 articles about (4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid 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:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 115495-43-7
(4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid

Guidance literature:: Multi-step reaction with 12 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

5: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

6: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

7: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

8: dimethoxypropane, conc. HCl / 1.5 h / Ambient temperature

9: 95 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

10: 92 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

11: sodium methoxide / methanol / 0.5 h / 0 °C

12: 1.) n-butyl lithium, hexamethyldisilazane / 1.) THF, 0 deg C, 15 min; 2.) THF, RT, 1 h, 3.) THF, RT, 15 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; nickel; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 99315-76-1
(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

: 115495-43-7
(4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / tetrahydrofuran / -78 °C

2: 85 percent / oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide / tetrahydrofuran / -78 °C

3: 65 percent / Raney nickel / tetrahydrofuran

4: NaBH₄ / tetrahydrofuran; H₂O

5: H⁽¹⁺⁾ / acetone

6: 62 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran

7: 92 percent / pyridine / 0 °C

8: 85 percent / NaOMe / methanol

9: tetrahydrofuran / 0 - 25 °C

With pyridine; sodium tetrahydroborate; MoO₅*pyridine*HMPA; tetrabutyl ammonium fluoride; sodium methylate; hydrogen cation; nickel; In tetrahydrofuran; methanol; water; acetone;

Reference yield:

: 92512-33-9
(3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one

: 115495-43-7
(4R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-2-phenylsulfanyl-hexanoic acid

Guidance literature:: Multi-step reaction with 14 steps

1: tetrahydrofuran / 0.25 h / Ambient temperature

2: Raney nickel / tetrahydrofuran / 4 h / Heating

3: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

4: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

5: 30percent H₂O₂ / 0 °C

6: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

7: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

8: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

9: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

10: dimethoxypropane, conc. HCl / 1.5 h / Ambient temperature

11: 95 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

12: 92 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

13: sodium methoxide / methanol / 0.5 h / 0 °C

14: 1.) n-butyl lithium, hexamethyldisilazane / 1.) THF, 0 deg C, 15 min; 2.) THF, RT, 1 h, 3.) THF, RT, 15 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; nickel; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(01)87683-3