(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide

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Chemical Name:(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide
CAS No.:182220-16-2
Molecular Formula:C₁₇H₂₀N₂O₇
Molecular Weight:364.355
Hs Code.:

Synonyms:(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide

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Chemical Property of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide

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Technology Process of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide

There total 8 articles about (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide 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: 79.0%

: 182369-08-0
(2S,3R,4R,4'R,5R)-6,8-diaza-3,4-dihydroxy-2-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-1-oxa-8-N-phenyl-spiro[4.4]nonane-7,9-dione

: 182220-16-2
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide

Guidance literature:: With potassium tert-butylate; In N,N-dimethyl-formamide; for 48h;
DOI:10.1016/0040-4020(96)00595-9

Reference yield: 13.0%

: 164905-93-5
(2R,3S,4R,4'R,5R)-6,8-diaza-3,4-di-tert-butyldimethylsilyloxy-2-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-1-oxa-8-N-phenyl-spiro<4.4>nonane-7,9-dione

: 182220-16-2
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide

: 182369-08-0
(2S,3R,4R,4'R,5R)-6,8-diaza-3,4-dihydroxy-2-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-1-oxa-8-N-phenyl-spiro[4.4]nonane-7,9-dione

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 21h;
DOI:10.1016/0040-4020(96)00595-9

Reference yield:

: 103-71-9
phenyl isocyanate

: 182220-16-2
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-oxo-tetrahydro-furo[2,3-d]oxazole-3a-carboxylic acid phenylamide

Guidance literature:: Multi-step reaction with 5 steps

1: 17 percent / tetrahydrofuran / 14 h

2: 88 percent / potassium tert-butoxide / dimethylformamide / 1 h

3: 75 percent / aq. trifluoroacetic acid / dioxane / 26 h

4: 76 percent / camphor sulfonic acid / 2.5 h

5: 79 percent / potassium tert-butoxide / dimethylformamide / 48 h

With camphor-10-sulfonic acid; potassium tert-butylate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(96)00595-9