(S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one

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Chemical Name:(S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one
CAS No.:709044-09-7
Molecular Formula:C₂₈H₃₃NO₅S₂
Molecular Weight:527.706
Hs Code.:

Synonyms:(S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one

There total 19 articles about (S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one 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: 84.3%

: 69152-87-0
4-benzyloxycrotonaldehyde

: 496784-31-7
(S)-4-Benzyl-3-[3-(2-methyl-[1,3]dithiolan-2-yl)-propionyl]-oxazolidin-2-one

: 709044-09-7
(S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one

Guidance literature:: (S)-4-Benzyl-3-[3-(2-methyl-[1,3]dithiolan-2-yl)-propionyl]-oxazolidin-2-one; With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; In dichloromethane; at 0 ℃; for 1h;

4-benzyloxycrotonaldehyde; In dichloromethane; at -78 ℃; for 1.5h;

Reference yield:

: 69152-87-0
4-benzyloxycrotonaldehyde

: 709044-09-7
(S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: TMEDA / CH₂Cl₂ / 2 h / 0 °C

1.2: 78.7 percent / CH₂Cl₂ / 0 °C

2.1: 96.7 percent / 2,6-lutidine / dimethylformamide / 24 h / 20 °C

3.1: 95.9 percent / LiBH₄ / diethyl ether; methanol; tetrahydrofuran / 0 °C

4.1: 95.8 percent / i-Pr₂NEt; Py*SO₂ / CH₂Cl₂; dimethylsulfoxide / 0.25 h / 0 °C

5.1: 97.8 percent / TsOH / methanol / 1 h / 20 °C

6.1: 97.1 percent / PPTS / benzene / Heating

7.1: 89.4 percent / NaHCO₃; I₂ / acetone; H₂O / 0.25 h / 0 °C

8.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

8.2: tetrahydrofuran; hexane / -78 - 20 °C

9.1: 2.25 g / TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

10.1: 97 percent / DBU / methanol / 1 h / 0 °C

11.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

11.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

11.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

12.1: 29 mg / L-Selectride / tetrahydrofuran / 1 h / -78 °C

13.1: TiCl₄; TMEDA / CH₂Cl₂ / 1 h / 0 °C

13.2: 84.3 percent / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; lithium borohydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodine; pyridinium p-toluenesulfonate; titanium tetrachloride; sulfur(IV) oxide * pyridine; L-Selectride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene; 11.3: Michael addition;

Reference yield:

: 664997-40-4
(E)-(2S,3R)-6-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-en-1-one

: 709044-09-7
(S)-4-Benzyl-3-[(E)-(2S,3R)-6-benzyloxy-3-hydroxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-hex-4-enoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 96.7 percent / 2,6-lutidine / dimethylformamide / 24 h / 20 °C

2.1: 95.9 percent / LiBH₄ / diethyl ether; methanol; tetrahydrofuran / 0 °C

3.1: 95.8 percent / i-Pr₂NEt; Py*SO₂ / CH₂Cl₂; dimethylsulfoxide / 0.25 h / 0 °C

4.1: 97.8 percent / TsOH / methanol / 1 h / 20 °C

5.1: 97.1 percent / PPTS / benzene / Heating

6.1: 89.4 percent / NaHCO₃; I₂ / acetone; H₂O / 0.25 h / 0 °C

7.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: tetrahydrofuran; hexane / -78 - 20 °C

8.1: 2.25 g / TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

9.1: 97 percent / DBU / methanol / 1 h / 0 °C

10.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

10.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

11.1: 29 mg / L-Selectride / tetrahydrofuran / 1 h / -78 °C

12.1: TiCl₄; TMEDA / CH₂Cl₂ / 1 h / 0 °C

12.2: 84.3 percent / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; lithium borohydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodine; pyridinium p-toluenesulfonate; titanium tetrachloride; sulfur(IV) oxide * pyridine; L-Selectride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene; 10.3: Michael addition;