(1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine

Base Information

• Chemical Name: (1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine
• CAS No.: 321577-01-9
• Molecular Formula: C₁₇H₂₀N₂O₇S
• Molecular Weight: 396.421

Synonyms:(1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine

Chemical Property of (1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine

There total 5 articles about (1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine 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: 88.0%

(1S,2R,3S)-N-(3-hydroxypropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine (321576-99-2) → (1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine (321577-01-9)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; In sodium hydrogencarbonate;

DOI:10.1016/S0040-4020(00)00895-4

Reference yield:

(3R,4R,5S)-3-hydroxy-4,5-(isopropylidenedioxy)-cyclopentene (185622-62-2) → (1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine (321577-01-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / Heating

2: 87 percent / TBAF / tetrahydrofuran

3: 88 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO); NaOCl; KBr / aq. NaHCO₃

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; potassium bromide; In tetrahydrofuran; sodium hydrogencarbonate; 1: Mitsunobu coupling / 2: desilylation / 3: Oxidation;

DOI:10.1016/S0040-4020(00)00895-4

Reference yield:

N-o-nitrobenzenesulfonyl-O-tert-butyldimethylsilyl-3-amino-1-propanol (321576-95-8) → (1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine (321577-01-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / Heating

2: 87 percent / TBAF / tetrahydrofuran

3: 88 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO); NaOCl; KBr / aq. NaHCO₃

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; potassium bromide; In tetrahydrofuran; sodium hydrogencarbonate; 1: Mitsunobu coupling / 2: desilylation / 3: Oxidation;

DOI:10.1016/S0040-4020(00)00895-4

upstream raw materials:

(1S,2R,3S)-N-(3-hydroxypropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine

(3R,4R,5S)-3-hydroxy-4,5-(isopropylidenedioxy)-cyclopentene

N-o-nitrobenzenesulfonyl-O-tert-butyldimethylsilyl-3-amino-1-propanol

N,O-bis(tert-butyldimethylsilyl)-N-o-nitrobenzenesulfonyl-3-amino-1-propanol

Downstream raw materials:

N-(2-bromo-3-oxo-propyl)-N-(2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-2-nitro-benzenesulfonamide

queuine

2-amino-5-[(1S,2R,3S)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylaminomethyl]-pyrrolo[2,3-d]pyrimidin-4(3H)-one

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