2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester
• CAS No.: 203796-09-2
• Molecular Formula: C₁₈H₁₉NO₆S
• Molecular Weight: 377.418

Synonyms:2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester

Chemical Property of 2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester

There total 8 articles about 2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl 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:

(2S,3S,4R)-2-(hydroxymethyl)tetrahydrofuran-3,4-diol (3169-91-3) → 2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester (203796-09-2)

Guidance literature:

Multi-step reaction with 5 steps

1: ZnCl₂ / 48 h / Ambient temperature

2: 49 percent / CrO₃, Ac₂O, pyridine / CH₂Cl₂ / 3 h / Ambient temperature

3: 66.5 percent / aq. NaHCO₃ / ethyl acetate / Ambient temperature

4: 40.5 percent / H₂S, 4-dimethylaminopyridine / ethanol; dioxane / 10 h / Ambient temperature

5: 73.5 percent / acetonitrile / 48 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; hydrogen sulfide; acetic anhydride; sodium hydrogencarbonate; zinc(II) chloride; In 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0957-4166(97)00615-0

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester (203796-09-2)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 2 h / Ambient temperature

2: TFA / 24 h / 80 °C

3: 0.3percent aq. TFA / 6 h / 80 °C

4: NaBH₄ / H₂O / 1.5 h / Ambient temperature

5: ZnCl₂ / 48 h / Ambient temperature

6: 49 percent / CrO₃, Ac₂O, pyridine / CH₂Cl₂ / 3 h / Ambient temperature

7: 66.5 percent / aq. NaHCO₃ / ethyl acetate / Ambient temperature

8: 40.5 percent / H₂S, 4-dimethylaminopyridine / ethanol; dioxane / 10 h / Ambient temperature

9: 73.5 percent / acetonitrile / 48 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; sodium tetrahydroborate; hydrogen sulfide; acetic anhydride; sodium hydrogencarbonate; trifluoroacetic acid; zinc(II) chloride; In 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0957-4166(97)00615-0

Reference yield:

(2R,3S,4R)-2-Dimethoxymethyl-tetrahydro-furan-3,4-diol (20701-46-6) → 2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester (203796-09-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 0.3percent aq. TFA / 6 h / 80 °C

2: NaBH₄ / H₂O / 1.5 h / Ambient temperature

3: ZnCl₂ / 48 h / Ambient temperature

4: 49 percent / CrO₃, Ac₂O, pyridine / CH₂Cl₂ / 3 h / Ambient temperature

5: 66.5 percent / aq. NaHCO₃ / ethyl acetate / Ambient temperature

6: 40.5 percent / H₂S, 4-dimethylaminopyridine / ethanol; dioxane / 10 h / Ambient temperature

7: 73.5 percent / acetonitrile / 48 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; sodium tetrahydroborate; hydrogen sulfide; acetic anhydride; sodium hydrogencarbonate; trifluoroacetic acid; zinc(II) chloride; In 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0957-4166(97)00615-0

upstream raw materials:

(2S,3S,4R)-2-(hydroxymethyl)tetrahydrofuran-3,4-diol

1,2-O-isopropylidene-α-D-xylose

(2R,3S,4R)-2-Dimethoxymethyl-tetrahydro-furan-3,4-diol

3,5-O-benzylidene-1,4-anhydro-L-xylitol

Downstream raw materials:

2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid methylamide

2-((2R,4aS,7R,7aR)-7-Hydroxy-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid amide

2-((2R,4aS,7R,7aR)-7-Fluoro-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-thiazole-4-carboxylic acid ethyl ester

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