Kifunensine diacetonide

Base Information

• Chemical Name: Kifunensine diacetonide
• CAS No.: 134234-43-8
• Molecular Formula: C₁₄H₂₀N₂O₆
• Molecular Weight: 312.323
• DSSTox Substance ID: DTXSID70469302
• Wikidata: Q82296962
• Mol file: 134234-43-8.mol

Synonyms:Kifunensine diacetonide;134234-43-8;(1R,6S,7R,11S,12R)-9,9,14,14-tetramethyl-8,10,13,15-tetraoxa-2,5-diazatetracyclo[10.4.0.02,6.07,11]hexadecane-3,4-dione;(3aS,3bR,7aR,11aS,11bR)-Hexahydro-2,2,5,5-tetramethyl-7H-[1,3]dioxino[4,5-e]-1,3-dioxolo[4,5-c]imidazo[1,2-a]pyridine-9,10-dione;DTXSID70469302;AKOS030254354;J-006503

Chemical Property of Kifunensine diacetonide

Chemical Property:

• Melting Point: >280°C
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 312.13213636
• Heavy Atom Count: 22
• Complexity: 548

Purity/Quality:

95% ^*data from raw suppliers

Kifunensine diacetonide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC2C(O1)C3C(C4N2C(=O)C(=O)N4)OC(O3)(C)C)C
• Isomeric SMILES: CC1(OC[C@@H]2[C@@H](O1)[C@H]3[C@@H]([C@@H]4N2C(=O)C(=O)N4)OC(O3)(C)C)C
• Uses: Precursor to Kifunensine.

Technology Process of Kifunensine diacetonide

There total 32 articles about Kifunensine diacetonide 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: 83.0%

kifunensine (109944-15-2) + 2,2-dimethoxy-propane (77-76-9) → (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dion-4-azaindolizidine (134234-43-8)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 12h;

DOI:10.1248/cpb.39.1378

Reference yield: 55.0%

5-Deoxy-2,3:4,6-di-O-isopropylidene-5-oxamoylamino-D-mannose (128741-70-8) → (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dion-4-azaindolizidine (134234-43-8)

Guidance literature:

With ammonia; In methanol; Ambient temperature;

DOI:10.1016/S0040-4039(00)94377-6

Reference yield:

5-deoxy-2,3:4,6-di-O-isopropylidene-2-oxamoylamino-D-mannose → (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dion-4-azaindolizidine (134234-43-8)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

upstream raw materials:

5-Deoxy-2,3:4,6-di-O-isopropylidene-5-oxamoylamino-D-mannose

kifunensine

2,2-dimethoxy-propane

2,2-Dimethyl-propionic acid (4R,5S)-5-((1R,2R)-2-azido-1,3-dihydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Downstream raw materials:

kifunensine

8a-epi-kifunensine