(1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane

Base Information

Chemical Name:(1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane
CAS No.:168773-68-0
Molecular Formula:C₂₁H₃₁NO₆S
Molecular Weight:425.546
Hs Code.:

Synonyms:(1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane

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Chemical Property of (1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane

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Technology Process of (1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane

There total 14 articles about (1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane 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: 69.0%

: 937-63-3
p-Tolyl chlorothionoformate

: 168773-62-4
(1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-hydroxy-4-<(methoxymethoxy)methyl>cyclopentane

: (3aR,5S,6aS)-5-Methoxymethoxymethyl-2-thioxo-tetrahydro-cyclopentaoxazole-3-carboxylic acid tert-butyl ester

: 168773-68-0
(1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane

Guidance literature:: With dmap; In acetonitrile; for 11.5h;
DOI:10.1021/jo00119a044

Reference yield:

: 168773-40-8
(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone

: 168773-68-0
(1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / H₂ / 10percent Pd/C / ethanol / 23 h

2: 93 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h

3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min

4: 99 percent / NH₃, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min

5: 100 percent / 4-DMAP, pyridine / 36 h

6: 98 percent / NaBH₄ / methanol / 2.5 h

7: 94 percent / DIEA / CH₂Cl₂ / 6 h

8: 100 percent / TBAF / tetrahydrofuran / 24 h

9: 69 percent / 4-DMAP / acetonitrile / 11.5 h

With pyridine; dmap; sodium tetrahydroborate; carbon tetrabromide; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00119a044

Reference yield:

: (6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone

: 168773-68-0
(1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane

Guidance literature:: Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 15 h

2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h

3: 100 percent / H₂ / 10percent Pd/C / ethanol / 23 h

4: 93 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h

5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min

6: 99 percent / NH₃, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min

7: 100 percent / 4-DMAP, pyridine / 36 h

8: 98 percent / NaBH₄ / methanol / 2.5 h

9: 94 percent / DIEA / CH₂Cl₂ / 6 h

10: 100 percent / TBAF / tetrahydrofuran / 24 h

11: 69 percent / 4-DMAP / acetonitrile / 11.5 h

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; carbon tetrabromide; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00119a044