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

Base Information

Chemical Name:(1R,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-hydroxycyclopentane
CAS No.:154494-88-9
Molecular Formula:C₃₂H₃₉NO₄Si
Molecular Weight:529.751
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 10 articles about (1R,2S,4S,5R)-1-<(9-Phenyl-9-fluorenyl)amino>-2-<(tert-butyldimethylsilyl)oxy>-4-(methoxycarbonyl)-5-hydroxycyclopentane 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: 86.0%

: (2S,3S)-2-<(9-Phenyl-9-fluorenyl)amino>-3-<(tert-butyldimethylsilyl)oxy>-5-(methoxycarbonyl)cyclopentanone

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

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

Guidance literature:: With sodium tetrahydroborate; In isopropyl alcohol; at 0 ℃; for 3h; Yield given;
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

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

Guidance literature:: Multi-step reaction with 10 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

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; hydrogen; oxygen; potassium hexamethylsilazane; potassium carbonate; 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

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

Guidance literature:: Multi-step reaction with 4 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

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