ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate

Base Information

Chemical Name:ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate
CAS No.:860642-22-4
Molecular Formula:C₂₀H₂₃NO₆S
Molecular Weight:405.472
Hs Code.:

Synonyms:ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate

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Chemical Property of ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate

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Technology Process of ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate

There total 4 articles about ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate 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: 50.0%

: 860642-21-3
3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose-4-thioamide

: 70-23-5
ethyl Bromopyruvate

: 860642-22-4
ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate

Guidance literature:: In acetonitrile; at 20 ℃; for 1h;
DOI:10.1081/CAR-200060396

Reference yield:

: 70492-77-2
3-O-benzyl-1,2-O-isopropylidene-α-D-ribopentadialdoximefuranose

: 860642-22-4
ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: N,N'-dicyclohexylcarbodiimide; triethylamine; CuSO₄*5H₂O / H₂O; CH₂Cl₂ / 2 h / 20 °C

2: 85 percent / 4-(dimethylamino)pyridine; hydrogen sulfide / CHCl₃ / 6.5 h / 30 °C

3: 50 percent / acetonitrile / 1 h / 20 °C

With dmap; hydrogen sulfide; copper(II) sulfate; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; chloroform; water; acetonitrile;
DOI:10.1081/CAR-200060396

Reference yield:

: 63593-02-2
3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

: 860642-22-4
ethyl 2-[(4R)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-C-yl]thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: hydroxylamine hydrochloride; pyridine / H₂O / 0.25 h / 20 °C

2: N,N'-dicyclohexylcarbodiimide; triethylamine; CuSO₄*5H₂O / H₂O; CH₂Cl₂ / 2 h / 20 °C

3: 85 percent / 4-(dimethylamino)pyridine; hydrogen sulfide / CHCl₃ / 6.5 h / 30 °C

4: 50 percent / acetonitrile / 1 h / 20 °C

With pyridine; dmap; hydrogen sulfide; hydroxylamine hydrochloride; copper(II) sulfate; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; chloroform; water; acetonitrile;
DOI:10.1081/CAR-200060396