1-Deoxy-1-nitro-L-iditol

Base Information

• Chemical Name: 1-Deoxy-1-nitro-L-iditol
• CAS No.: 105499-37-4
• Molecular Formula: C₆H₁₃NO₇
• Molecular Weight: 211.172
• DSSTox Substance ID: DTXSID201318836
• Mol file: 105499-37-4.mol

Synonyms:105499-37-4;1-Deoxy-1-nitro-L-iditol;DTXSID201318836;(2S,3R,4R,5S)-6-Nitrohexane-1,2,3,4,5-pentaol

Chemical Property of 1-Deoxy-1-nitro-L-iditol

Chemical Property:

• XLogP3: -3.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 211.06920175
• Heavy Atom Count: 14
• Complexity: 182

Purity/Quality:

98% ^*data from raw suppliers

1-Deoxy-1-nitro-L-iditol hemihydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(C(C(CO)O)O)O)O)[N+](=O)[O-]
• Isomeric SMILES: C([C@@H]([C@H]([C@@H]([C@H](CO)O)O)O)O)[N+](=O)[O-]

Technology Process of 1-Deoxy-1-nitro-L-iditol

There total 1 articles about 1-Deoxy-1-nitro-L-iditol 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: 61.0%

nitromethane (75-52-5) + L-arabinose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (2S,3S,4S)-6-Nitro-hexane-1,2,3,4,5-pentaol (6027-42-5,14199-83-8,14199-88-3,20971-06-6,69257-51-8,74183-68-9,94481-72-8,96613-89-7,97466-53-0,97907-36-3,105499-37-4,107080-35-3,107080-36-4,114612-65-6,114612-66-7,120019-25-2)

Guidance literature:

With sodium methylate; In methanol; for 50h;

DOI:10.1021/jo00174a028

Reference yield:

(2S,3S,4S)-6-Nitro-hexane-1,2,3,4,5-pentaol (6027-42-5,14199-83-8,14199-88-3,20971-06-6,69257-51-8,74183-68-9,94481-72-8,96613-89-7,97466-53-0,97907-36-3,105499-37-4,107080-35-3,107080-36-4,114612-65-6,114612-66-7,120019-25-2) → 2,3;5,6-di-O-isopropylidene-L-mannofuranose + 1,2:5,6-di-O-isopropylidene-α-L-glucofuranose (582-52-5,2595-05-3,10368-86-2,13100-30-6,14686-89-6,23262-79-5,26597-74-0,26623-15-4,38166-58-4,38166-60-8,79943-22-9,83730-28-3)

Guidance literature:

(2S,3S,4S)-6-Nitro-hexane-1,2,3,4,5-pentaol; With sulfuric acid; In water;

In acetone; for 0.833333h; Irradiation;

DOI:10.3998/ark.5550190.0018.400

Reference yield:

(2S,3S,4S)-6-Nitro-hexane-1,2,3,4,5-pentaol (6027-42-5,14199-83-8,14199-88-3,20971-06-6,69257-51-8,74183-68-9,94481-72-8,96613-89-7,97466-53-0,97907-36-3,105499-37-4,107080-35-3,107080-36-4,114612-65-6,114612-66-7,120019-25-2) → C8H12O5

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid / water

1.2: 0.83 h / Irradiation

2.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane

3.1: sodium tetrahydroborate; ethanol / Cooling with ice

4.1: periodic acid / ethyl acetate

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; ethanol; sulfuric acid; acetic anhydride; periodic acid; In dichloromethane; water; ethyl acetate;

DOI:10.3998/ark.5550190.0018.400

upstream raw materials:

nitromethane

L-arabinose

Downstream raw materials:

1,2:5,6-di-O-isopropylidene-α-L-glucofuranose

Refernces