5-(azidomethyl)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol

Base Information

• Chemical Name: 5-(azidomethyl)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol
• CAS No.: 126210-25-1
• Molecular Formula: C9H15N3O5
• Molecular Weight: 245.235
• Mol file: 126210-25-1.mol

Synonyms:126210-25-1;6-Azido-6-deoxy-2,3-O-isopropylidene-a-L-sorbofuranose

Chemical Property of 5-(azidomethyl)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol

Chemical Property:

• Appearance/Colour: clear liquid
• PSA: 117.90000
• LogP: -0.65074
• Solubility.: Dichloromethane
• Water Solubility.: Soluble in Dichloromethane
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 245.10117059
• Heavy Atom Count: 17
• Complexity: 357

Purity/Quality:

99% ^*data from raw suppliers

6-Azido-6-deoxy-2,3-O-isopropylidene-a-L-sorbofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2(O1)CO)CN=[N+]=[N-])O)C

Technology Process of 5-(azidomethyl)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol

There total 2 articles about 5-(azidomethyl)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol 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: 80.0%

2,3-O-isopropylidene-α-L-sorbofuranose (17682-71-2) → 6-azido-6-desoxy-2,3-O-isopropylidene-α-L-sorbofuranose (126210-25-1)

Guidance literature:

With lithium azide; carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide; at 120 ℃; for 24h;

DOI:10.1016/0008-6215(89)85058-X

Reference yield:

L-sorbose (35673-97-3) → 6-azido-6-desoxy-2,3-O-isopropylidene-α-L-sorbofuranose (126210-25-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent

2: 80 percent / LiN₃, triphenylphosphine, CBr₄, / dimethylformamide / 24 h / 120 °C

With lithium azide; carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)85058-X

Reference yield:

6-azido-6-desoxy-2,3-O-isopropylidene-α-L-sorbofuranose (126210-25-1) → 1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Dowex 50X₈-100, / H₂O / 4 h / 60 °C

2: H₂, / PtO₂*2H₂O/C, / 0.25 h / 75006 Torr / Ambient temperature

With Dowex 50x8-100; hydrogen; platinum(IV) oxide; In water;

DOI:10.1016/0008-6215(89)85058-X

upstream raw materials:

2,3-O-isopropylidene-α-L-sorbofuranose

L-sorbose

Downstream raw materials:

1,5-dideoxy-1,5-imino-D-glucitol

6-(benzyloxycarbonyl)amino-6-desoxy-2,3-O-isopropylidene-α-L-sorbofuranose