(4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester
CAS No.:475291-35-1
Molecular Formula:C₂₇H₃₃NO₁₀S
Molecular Weight:563.626
Hs Code.:

Synonyms:(4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

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Chemical Property of (4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

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Technology Process of (4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

There total 21 articles about (4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl 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:

: 124-63-0
methanesulfonyl chloride

: 386765-92-0
methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate

: 475291-35-1
(4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 25 ℃; for 0.5h;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 386765-82-8
2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester

: 475291-35-1
(4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: K₂CO₃ / xylene / 60 h / 140 °C

1.2: ozone / methanol / 0.25 h / -78 °C

1.3: 486 mg / Me₂S / methanol / -78 - 0 °C

2.1: NaH₂PO₄*2H₂O; HOSO₂NH₂; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 0.25 h / 25 °C

3.1: 405 mg / methanol / 1 h / 25 °C

4.1: 76 percent / aqueous HCl / tetrahydrofuran / 10 h / 25 °C

5.1: 89 percent / toluene / 20 h / 25 °C

6.1: 82 percent / DIBAL-H / tetrahydrofuran; toluene / 0.25 h / -18 °C

7.1: 86 percent / DBU / CH₂Cl₂ / 20 h / 25 °C

8.1: triethylamine / CH₂Cl₂ / 0.5 h / 25 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; amidosulfuric acid fluoride; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; xylene; tert-butyl alcohol; 1.1: Overman rearrangement;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 386765-87-3
methyl (S)-2-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-3-(4-methoxybenzyloxy)-2-(trichloroacetamido)propanoate

: 475291-35-1
(4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / aqueous HCl / tetrahydrofuran / 10 h / 25 °C

2: 89 percent / toluene / 20 h / 25 °C

3: 82 percent / DIBAL-H / tetrahydrofuran; toluene / 0.25 h / -18 °C

4: 86 percent / DBU / CH₂Cl₂ / 20 h / 25 °C

5: triethylamine / CH₂Cl₂ / 0.5 h / 25 °C

With hydrogenchloride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1246/bcsj.75.1927