(1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

Base Information

Chemical Name:(1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one
CAS No.:203935-00-6
Molecular Formula:C₁₇H₂₃NO₄
Molecular Weight:305.374
Hs Code.:

Synonyms:(1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

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Chemical Property of (1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

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Technology Process of (1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

There total 11 articles about (1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 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:

: (1S,6R,7S,7aS)-6-Benzyl-7a-(tert-butyl-dimethyl-silanyloxymethyl)-7-hydroxy-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 203935-00-6
(1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 23 ℃; for 24h; Yield given;
DOI:10.1021/ja973444c

Reference yield:

: 145451-90-7
(2R,4R)-3-Benzyl-2-tert-butyl-4-((S)-1-hydroxy-2-methyl-propyl)-oxazolidine-4-carboxylic acid methyl ester

: 203935-00-6
(1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

Guidance literature:: Multi-step reaction with 8 steps

1: trifluoromethanesulfonic acid / methanol; H₂O / 6.5 h / 80 - 85 °C

2: imidazole / dimethylformamide / 25 h / 23 °C

3: p-TsOH*H₂O / benzene / 0.5 h / 80 °C

4: LiBH₄ / tetrahydrofuran; methanol / 20 h / 23 °C

5: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 2 h / -78 °C

6: 1.) MgI₂, 3.) K₂CO₃

7: 1.) i-Pr₂NEt, H₂ / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h

8: 48percent HF / acetonitrile / 24 h / 23 °C

With 1H-imidazole; lithium borohydride; oxalyl dichloride; trifluorormethanesulfonic acid; hydrogen fluoride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; magnesium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ja973444c

Reference yield:

: 145452-01-3
[(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-methanol

: 203935-00-6
(1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

Guidance literature:: Multi-step reaction with 4 steps

1: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 2 h / -78 °C

2: 1.) MgI₂, 3.) K₂CO₃

3: 1.) i-Pr₂NEt, H₂ / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h

4: 48percent HF / acetonitrile / 24 h / 23 °C

With oxalyl dichloride; hydrogen fluoride; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; magnesium iodide; palladium on activated charcoal; In dichloromethane; acetonitrile;
DOI:10.1021/ja973444c