(2S,3S,4S)-3-Hydroxy-2-methyl-4-((4R,5R)-2,2,5-trimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-pentanethioic acid S-tert-butyl ester

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Chemical Name:(2S,3S,4S)-3-Hydroxy-2-methyl-4-((4R,5R)-2,2,5-trimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-pentanethioic acid S-tert-butyl ester
CAS No.:118974-96-2
Molecular Formula:C₃₆H₄₆O₅S
Molecular Weight:590.824
Hs Code.:

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Chemical Property of (2S,3S,4S)-3-Hydroxy-2-methyl-4-((4R,5R)-2,2,5-trimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-pentanethioic acid S-tert-butyl ester

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Technology Process of (2S,3S,4S)-3-Hydroxy-2-methyl-4-((4R,5R)-2,2,5-trimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-pentanethioic acid S-tert-butyl ester

There total 11 articles about (2S,3S,4S)-3-Hydroxy-2-methyl-4-((4R,5R)-2,2,5-trimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-pentanethioic acid S-tert-butyl ester 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:

: 81247-60-1
(2R,3R)-3-Hydroxy-2-methyl-3-((S)-2-methyl-oxiranyl)-propionic acid benzyl ester

: 118974-96-2
(2S,3S,4S)-3-Hydroxy-2-methyl-4-((4R,5R)-2,2,5-trimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-pentanethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / 10percent Pd-C / methanol / Ambient temperature

2: 4-dimethylaminopyridine / pyridine / 50 °C

3: LiBH₄ / tetrahydrofuran / Heating

4: pyridinium p-toluenesulfonate, CuSO₄ / Ambient temperature

5: DMSO-(COCl)2, Et₃N / CH₂Cl₂ / -78 °C

6: lithium diisopropylamide / tetrahydrofuran / -100 °C

With dmap; lithium borohydride; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; copper(II) sulfate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane;
DOI:10.1016/S0040-4039(00)86716-7

Reference yield:

: 118975-20-5
(R)-1-((S)-4-Isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-pent-4-ene-1,3-dione

: 118974-96-2
(2S,3S,4S)-3-Hydroxy-2-methyl-4-((4R,5R)-2,2,5-trimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-pentanethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 69 percent / Zn(BH₄)2 / CH₂Cl₂ / -20 - -10 °C

2: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

3: tetrahydrofuran / -20 - 0 °C

4: pyridinium p-toluenesulfonate / ethanol / 50 °C

5: t-BuOOH / VO(acac)2 / toluene / -20 - 0 °C

6: H₂ / 10percent Pd-C / methanol / Ambient temperature

7: 4-dimethylaminopyridine / pyridine / 50 °C

8: LiBH₄ / tetrahydrofuran / Heating

9: pyridinium p-toluenesulfonate, CuSO₄ / Ambient temperature

10: DMSO-(COCl)2, Et₃N / CH₂Cl₂ / -78 °C

11: lithium diisopropylamide / tetrahydrofuran / -100 °C

With tert.-butylhydroperoxide; dmap; lithium borohydride; zinc(II) tetrahydroborate; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; copper(II) sulfate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; toluene;
DOI:10.1016/S0040-4039(00)86716-7

Reference yield:

: 118975-00-1
(S)-3-((2R,3R)-3-Hydroxy-2,4-dimethyl-pent-4-enoyl)-4-isopropyl-oxazolidin-2-one

: 118974-96-2
(2S,3S,4S)-3-Hydroxy-2-methyl-4-((4R,5R)-2,2,5-trimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-pentanethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

2: tetrahydrofuran / -20 - 0 °C

3: pyridinium p-toluenesulfonate / ethanol / 50 °C

4: t-BuOOH / VO(acac)2 / toluene / -20 - 0 °C

5: H₂ / 10percent Pd-C / methanol / Ambient temperature

6: 4-dimethylaminopyridine / pyridine / 50 °C

7: LiBH₄ / tetrahydrofuran / Heating

8: pyridinium p-toluenesulfonate, CuSO₄ / Ambient temperature

9: DMSO-(COCl)2, Et₃N / CH₂Cl₂ / -78 °C

10: lithium diisopropylamide / tetrahydrofuran / -100 °C

With tert.-butylhydroperoxide; dmap; lithium borohydride; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; copper(II) sulfate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; toluene;
DOI:10.1016/S0040-4039(00)86716-7