(2R,3R,4S,5S)-2-(Hydroxymethyl)-5-(4-nitrophenyl)pyrrolidine-3,4-diol

Base Information

• Chemical Name: (2R,3R,4S,5S)-2-(Hydroxymethyl)-5-(4-nitrophenyl)pyrrolidine-3,4-diol
• CAS No.: 188745-01-9
• Molecular Formula: C₁₁H₁₄N₂O₅
• Molecular Weight: 254.243
• Nikkaji Number: J823.327F
• Mol file: 188745-01-9.mol

Synonyms:(2R,3R,4S,5S)-2-(Hydroxymethyl)-5-(4-nitrophenyl)pyrrolidine-3,4-diol;188745-01-9;SCHEMBL8119256

Chemical Property of (2R,3R,4S,5S)-2-(Hydroxymethyl)-5-(4-nitrophenyl)pyrrolidine-3,4-diol

Chemical Property:

• PSA: 118.54000
• LogP: 0.17380
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 254.09027155
• Heavy Atom Count: 18
• Complexity: 300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2C(C(C(N2)CO)O)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1[C@H]2[C@@H]([C@@H]([C@H](N2)CO)O)O)[N+](=O)[O-]

Technology Process of (2R,3R,4S,5S)-2-(Hydroxymethyl)-5-(4-nitrophenyl)pyrrolidine-3,4-diol

There total 10 articles about (2R,3R,4S,5S)-2-(Hydroxymethyl)-5-(4-nitrophenyl)pyrrolidine-3,4-diol 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: 71.0%

→ 1,4-Dideoxy-1,4-imino-1-(S)-(4-nitrophenyl)-D-ribitol (188745-01-9)

Guidance literature:

Reference yield:

N,N-diallyl-4-bromobenzenamine (30438-95-0) → 1,4-Dideoxy-1,4-imino-1-(S)-(4-nitrophenyl)-D-ribitol (188745-01-9)

Guidance literature:

Multi-step reaction with 6 steps

1: BuLi / diethyl ether; hexane / 0.5 h / Ambient temperature

2: 60 percent / tetrahydrofuran; diethyl ether; hexane / 1.) -78 deg C, 30 min, 2.) room temperature, 30 min

3: 99 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h

4: 63 percent / (Ph₃P)3RhCl / acetonitrile; H₂O / 4 h / Heating

5: 74 percent / NaHCO₃, oxone / acetone; H₂O / 1.) 5 deg C, 1 h, 2.) room temperature, 1 h

6: 1.) 3M HCl, 2.) Amberlyst A 26 (OH^- form) / 1.) MeOH, H₂O, room temperature, 3 h, 2.) MeOH, H₂O

With hydrogenchloride; Oxone; Wilkinson's catalyst; n-butyllithium; Amberlyst A 26 (OH^- form); sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0040-4020(96)01172-6

Reference yield:

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-31-7) → 1,4-Dideoxy-1,4-imino-1-(S)-(4-nitrophenyl)-D-ribitol (188745-01-9)

Guidance literature:

Multi-step reaction with 7 steps

1: NCS / pentane / 0.5 h / Ambient temperature

2: 1.) BuLi, 2,2,6,6-tetramethylpiperidine / 1.) THF, 0 deg C, 2.) THF, -78 deg C

3: 60 percent / tetrahydrofuran; diethyl ether; hexane / 1.) -78 deg C, 30 min, 2.) room temperature, 30 min

4: 99 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h

5: 63 percent / (Ph₃P)3RhCl / acetonitrile; H₂O / 4 h / Heating

6: 74 percent / NaHCO₃, oxone / acetone; H₂O / 1.) 5 deg C, 1 h, 2.) room temperature, 1 h

7: 1.) 3M HCl, 2.) Amberlyst A 26 (OH^- form) / 1.) MeOH, H₂O, room temperature, 3 h, 2.) MeOH, H₂O

With 2,2,6,6-tetramethyl-piperidine; hydrogenchloride; Oxone; N-chloro-succinimide; Wilkinson's catalyst; n-butyllithium; Amberlyst A 26 (OH^- form); sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile; pentane;

DOI:10.1016/S0040-4020(96)01172-6

upstream raw materials:

(3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-(4-nitro-phenyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

N,N-diallyl-4-bromobenzenamine

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

(3aR,4R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-chloro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole