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

Base Information

• Chemical Name: (1S,2R,3S)-N-(3-tert-butyldimethylsilyloxypropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine
• CAS No.: 321576-97-0
• Molecular Formula: C₂₃H₃₆N₂O₇SSi
• Molecular Weight: 512.7
• Mol file: 321576-97-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (1S,2R,3S)-N-(3-tert-butyldimethylsilyloxypropyl)-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: 77.0%

(3R,4R,5S)-3-hydroxy-4,5-(isopropylidenedioxy)-cyclopentene (185622-62-2) + N-o-nitrobenzenesulfonyl-O-tert-butyldimethylsilyl-3-amino-1-propanol (321576-95-8) → (1S,2R,3S)-N-(3-tert-butyldimethylsilyloxypropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine (321576-97-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 24h; Heating;

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

Reference yield:

N,O-bis(tert-butyldimethylsilyl)-3-amino-1-propanol (162147-07-1) → (1S,2R,3S)-N-(3-tert-butyldimethylsilyloxypropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine (321576-97-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h

2: 71 percent / NH₄F / methanol / 0.5 h

3: 77 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / Heating

With dmap; ammonium fluoride; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1: sulfonylation / 2: desilylation / 3: Mitsunobu coupling;

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

Reference yield:

N,O-bis(tert-butyldimethylsilyl)-N-o-nitrobenzenesulfonyl-3-amino-1-propanol (321576-93-6) → (1S,2R,3S)-N-(3-tert-butyldimethylsilyloxypropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine (321576-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NH₄F / methanol / 0.5 h

2: 77 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / Heating

With ammonium fluoride; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; methanol; 1: desilylation / 2: Mitsunobu coupling;

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

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

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

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

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