N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide

Base Information

Chemical Name:N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide
CAS No.:118560-83-1
Molecular Formula:C₁₈H₂₂N₂O₅S
Molecular Weight:378.449
Hs Code.:

Synonyms:N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide

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Chemical Property of N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide

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Technology Process of N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide

There total 5 articles about N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide 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: 19.0%

: 118575-03-4
methyl 5-amino-2-O-benzyloxy-5-deoxy-5-(2-thiazolyl)-α-xylofuranoside

: 75-36-5
acetyl chloride

: 118560-83-1
N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide

: 118560-85-3
Acetic acid (2R,3S,4R,5R)-2-((R)-acetylamino-thiazol-2-yl-methyl)-4-benzyloxy-5-methoxy-tetrahydro-furan-3-yl ester

Guidance literature:: With triethylamine; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(01)85954-8

Reference yield:

: 118560-75-1
3-(2-thiazolyl)-3a,6a-dihydrofuro<2,3-d>isoxazole

: 118560-83-1
N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: m-chloroperbenzoic acid / methanol / 20 h / Ambient temperature

2: aluminium oxide / diethyl ether

3: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, reflux, 20 min, 2.) THF, 2 h

4: 78 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature

5: 66 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

With aluminum oxide; lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)85954-8

Reference yield:

: (1aS,1bR,4aS,5aR)-4-Thiazol-2-yl-1a,1b,4a,5a-tetrahydro-1,2,5-trioxa-3-aza-cyclopropa[a]pentalene

: 118560-83-1
N-[(S)-((2S,3R,4S,5S)-4-Benzyloxy-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-thiazol-2-yl-methyl]-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1: aluminium oxide / diethyl ether

2: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, reflux, 20 min, 2.) THF, 2 h

3: 78 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature

4: 66 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

With aluminum oxide; lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)85954-8