5-Azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone

Base Information

• Chemical Name: 5-Azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone
• CAS No.: 122194-04-1
• Molecular Formula: C8H11N3O4
• Molecular Weight: 213.19064
• DSSTox Substance ID: DTXSID80595343
• Wikidata: Q82490340
• Mol file: 122194-04-1.mol

Synonyms:122194-04-1;5-Azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone;(3aS,6R,6aS)-6-(azidomethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one;DTXSID80595343;(3aS,6R,6aS)-6-(azidomethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one;(3aS,6R,6aS)-6-(Azidomethyl)-2,2-dimethyldihydro-2H-furo[3,4-d][1,3]dioxol-4(3aH)-one

Chemical Property of 5-Azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone

Chemical Property:

• PSA: 94.51000
• LogP: 0.19496
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 213.07495584
• Heavy Atom Count: 15
• Complexity: 337

Purity/Quality:

99% ^*data from raw suppliers

5-Azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(=O)C2O1)CN=[N+]=[N-])C
• Isomeric SMILES: CC1(O[C@H]2[C@H](OC(=O)[C@H]2O1)CN=[N+]=[N-])C
• Uses: Intermediate in the production of Deoxyfuconojirimycin

Technology Process of 5-Azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone

There total 4 articles about 5-Azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone 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: 89.0%

2,3-O-isopropylidene-D-lyxono-1,4-lactone (56543-10-3) → 5-azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone (122194-04-1)

Guidance literature:

2,3-O-isopropylidene-D-lyxono-1,4-lactone; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane;

With sodium azide; In N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2005.10.002

Reference yield: 89.0%

Trifluoro-methanesulfonic acid (3aS,4R,6aS)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (122194-03-0) → 5-azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone (122194-04-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 0 ℃;

Reference yield:

D-lyxono-1,4-lactone (15384-34-6) → 5-azido-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,4-lactone (122194-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 60 percent / CuSO₄ / acetone

2.1: Tf₂O; pyridine / CH₂Cl₂

2.2: 89 percent / NaN₃ / dimethylformamide

With pyridine; trifluoromethylsulfonic anhydride; copper(II) sulfate; In dichloromethane; acetone;

DOI:10.1016/j.carres.2005.10.002

upstream raw materials:

Trifluoro-methanesulfonic acid (3aS,4R,6aS)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

2,3-O-isopropylidene-D-lyxono-1,4-lactone

D-lyxono-1,4-lactone

D-Galactose

Downstream raw materials:

deoxyfuconojirimycin

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