(4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:310441-20-4
Molecular Formula:C₂₄H₃₈N₂O₅S
Molecular Weight:466.642
Hs Code.:

Synonyms:(4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 9 articles about (4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid 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:

: (4S,5R)-4-Benzyl-5-{[(E)-(S)-1-methoxycarbonyl-3-methylsulfanyl-propylimino]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 310441-20-4
(4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃; for 2h;
DOI:10.1021/jo001072b

Reference yield:

: 63-91-2,25191-15-5,658-69-5,67675-33-6
L-phenylalanine

: 310441-20-4
(4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: LiAlH₄ / tetrahydrofuran

2: CH₂Cl₂

3: (COCl)2; DMSO; iPr₂NEt / CH₂Cl₂ / -35 - 0 °C

4: 2.7 g / tetrahydrofuran / 2 h / 20 °C

5: 85 percent / PPTS / toluene / 4 h / 80 °C

6: 2.7 g / OsO₄; NMO / acetone; H₂O; toluene / 8 h

7: 2.31 g / NaIO₄/SiO₂ / CH₂Cl₂ / 1 h / 0 °C

8: Na₂SO₄ / CH₂Cl₂ / 1 h / 0 - 20 °C

9: NaBH₄ / methanol / 2 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; oxalyl dichloride; pyridinium p-toluenesulfonate; silica gel; dimethyl sulfoxide; sodium sulfate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 1: Reduction / 2: Acylation / 3: Oxidation / 4: Grignard reaction / 5: Cyclization / 6: dihydroxylation / 7: oxidative cleavage / 8: Condensation / 9: Reduction;
DOI:10.1021/jo001072b

Reference yield:

: 3182-95-4
L-Phenylalaninol

: 310441-20-4
(4S,5S)-4-Benzyl-5-[((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: CH₂Cl₂

2: (COCl)2; DMSO; iPr₂NEt / CH₂Cl₂ / -35 - 0 °C

3: 2.7 g / tetrahydrofuran / 2 h / 20 °C

4: 85 percent / PPTS / toluene / 4 h / 80 °C

5: 2.7 g / OsO₄; NMO / acetone; H₂O; toluene / 8 h

6: 2.31 g / NaIO₄/SiO₂ / CH₂Cl₂ / 1 h / 0 °C

7: Na₂SO₄ / CH₂Cl₂ / 1 h / 0 - 20 °C

8: NaBH₄ / methanol / 2 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; pyridinium p-toluenesulfonate; silica gel; dimethyl sulfoxide; sodium sulfate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 1: Acylation / 2: Oxidation / 3: Grignard reaction / 4: Cyclization / 5: dihydroxylation / 6: oxidative cleavage / 7: Condensation / 8: Reduction;
DOI:10.1021/jo001072b