(1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>cyclopentane

Base Information

Chemical Name:(1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>cyclopentane
CAS No.:154494-89-0
Molecular Formula:C₃₃H₄₁NO₆SSi
Molecular Weight:607.843
Hs Code.:

Synonyms:(1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>cyclopentane

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Chemical Property of (1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>cyclopentane

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Technology Process of (1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>cyclopentane

There total 11 articles about (1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>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: 97.0%

: 124-63-0
methanesulfonyl chloride

: 154494-88-9
(1R,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-hydroxycyclopentane

: 154494-89-0
(1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>cyclopentane

Guidance literature:: With triethylamine; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/jo00081a019

Reference yield:

: 133473-09-3
methyl 2-[(9-phenylfluoren-9-yl)amino]-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate

: 154494-89-0
(1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>cyclopentane

Guidance literature:: Multi-step reaction with 11 steps

1: 86 percent / aq. HCl / diethyl ether / 3 h / 0 °C

2: 60 percent / O₂ / Pt / H₂O; ethyl acetate; propan-2-ol / 40 °C

3: 98 percent / K₂CO₃ / dimethylformamide / 12 h / Ambient temperature

4: pyridine / CH₂Cl₂ / 1 h

5: LiI*3H₂O / tetrahydrofuran; acetic acid / 48 h / Heating

6: 97 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C

7: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

8: 92 percent / H₂ / 10percent Pt/C / ethyl acetate / 15 h / 2068.6 Torr

9: 95 percent / KHMDS / tetrahydrofuran / 0.5 h / -78 °C

10: 86 percent / NaBH₄ / propan-2-ol / 3 h / 0 °C

11: 97 percent / Et₃N / tetrahydrofuran / 2 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; hydrogen; oxygen; potassium hexamethylsilazane; potassium carbonate; triethylamine; lithium iodide; platinum on activated charcoal; platinum; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo00081a019

Reference yield:

: Dimethyl (2S,3S)-(E)-2-<(9-phenyl-9-fluorenyl)amino>-3-hydroxy-4-hexenedioate

: 154494-89-0
(1S,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-<(methanesulfonyl)oxy>cyclopentane

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 92 percent / H₂ / 10percent Pt/C / ethyl acetate / 15 h / 2068.6 Torr

3: 95 percent / KHMDS / tetrahydrofuran / 0.5 h / -78 °C

4: 86 percent / NaBH₄ / propan-2-ol / 3 h / 0 °C

5: 97 percent / Et₃N / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; hydrogen; potassium hexamethylsilazane; triethylamine; platinum on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo00081a019