2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl fluoride

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl fluoride
• CAS No.: 2823-44-1
• Molecular Formula: C₁₄H₁₉FO₉
• Molecular Weight: 350.298
• European Community (EC) Number: 608-179-2
• DSSTox Substance ID: DTXSID40460700
• Nikkaji Number: J755.107J
• Mol file: 2823-44-1.mol

Synonyms:2823-44-1;2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL FLUORIDE;Acetofluoro-alpha-D-mannose;[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-fluorooxan-2-yl]methyl acetate;MFCD00792706;(2R,3R,4S,5S,6R)-2-(Acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate;tetra-o-acetyl-alpha-d-mannopyranosyl fluoride;Acetofluoro- alpha -D-mannose;SCHEMBL2037245;DTXSID40460700;JJXATNWYELAACC-DGTMBMJNSA-N;2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYLFLUORIDE;AC8160;AKOS015912717;BS-28127;Tetra-O-acetyl--D-mannopyranosyl fluoride;(2R,3R,4S,5S,6R)-2-(Acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyltriacetate;[(2R, 3R, 4S, 5S, 6R)-3, 4, 5-triacetyloxy-6-fluorooxan-2-yl]methyl acetate;[(2R,3R,4S,5S,6R)-3,4,5-TRIS(ACETYLOXY)-6-FLUOROOXAN-2-YL]METHYL ACETATE

Chemical Property of 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl fluoride

Chemical Property:

• Vapor Pressure: 8.11E-06mmHg at 25°C
• Storage Temp.: −20°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 350.10131034
• Heavy Atom Count: 24
• Complexity: 507

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-D-mannopyranosyl Fluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)F)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)F)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl fluoride

There total 87 articles about 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl fluoride 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: 99.0%

β-D-glucose pentaacetate (604-69-3) → 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose (439-03-2,439-04-3,439-05-4,2823-44-1,2823-46-3,3934-29-0,4163-44-4,4163-45-5,20409-31-8,23235-96-3,51897-75-7,51897-76-8,51897-77-9,57573-38-3,62561-28-8,126641-47-2)

Guidance literature:

With pyridine hydrogenfluoride; In dichloromethane; for 3h; cooling; polyethylene vessel !;

Reference yield: 95.0%

p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (28244-94-2,28244-99-7,86782-41-4,131488-65-8) → 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose (439-03-2,439-04-3,439-05-4,2823-44-1,2823-46-3,3934-29-0,4163-44-4,4163-45-5,20409-31-8,23235-96-3,51897-75-7,51897-76-8,51897-77-9,57573-38-3,62561-28-8,126641-47-2)

Guidance literature:

With ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In 1,2-dichloro-ethane; for 0.25h; Inert atmosphere; Reflux;

DOI:10.1016/j.carres.2012.04.016

Reference yield: 94.0%

2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate (439-03-2,439-04-3,439-05-4,2823-44-1,2823-46-3,3934-29-0,4163-44-4,4163-45-5,20409-31-8,23235-96-3,51897-75-7,51897-76-8,51897-77-9,57573-38-3,62561-28-8,126641-47-2) → 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose (439-03-2,439-04-3,439-05-4,2823-44-1,2823-46-3,3934-29-0,4163-44-4,4163-45-5,20409-31-8,23235-96-3,51897-75-7,51897-76-8,51897-77-9,57573-38-3,62561-28-8,126641-47-2)

Guidance literature:

silver tetrafluoroborate; In dichloromethane; at 10 ℃;

DOI:10.1016/0008-6215(84)85232-5

upstream raw materials:

β-D-mannopyranose pentaacetate

2,3,4,6-tetra-O-acetyl-D-mannopyranose

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

β-1-deoxy-1-C-(phenylthio)-2,3,4,5-tetra-O-acetyl-D-mannopyranose

Downstream raw materials:

N^α-fluoren-9-ylmethoxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-threonine benzyl ester

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl fluoride

4-bromophenyl α-D-mannopyranoside

2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl fluoride