2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl Fluoride

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl Fluoride
• CAS No.: 3934-29-0
• Molecular Formula: C₁₄H₁₉FO₉
• Molecular Weight: 350.298
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID50456770
• Nikkaji Number: J680.324E
• Wikidata: Q72504498
• Mol file: 3934-29-0.mol

Synonyms:3934-29-0;2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl Fluoride;(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate;[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-fluorooxan-2-yl]methyl acetate;C14H19FO9;MFCD00792705;Acetofluoro-alpha-D-glucose;Acetofluoro- alpha -D-glucose;SCHEMBL2215629;JJXATNWYELAACC-RGDJUOJXSA-;DTXSID50456770;AKOS015896833;(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyltriacetate;AS-69551;T1995;.alpha.-D-Glucopyranosyl fluoride, tetraacetate;T72420;Glucopyranosyl fluoride, tetraacetate, .alpha.-D-;1-Fluoro-1-deoxy-alpha-D-glucopyranose tetraacetate;[(2R,3R,4S,5R,6R)-3,4,5-TRIS(ACETYLOXY)-6-FLUOROOXAN-2-YL]METHYL ACETATE;InChI=1/C14H19FO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14+/m1/s1

Chemical Property of 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl Fluoride

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 105.0 to 109.0 °C
• Refractive Index: 1.465
• Boiling Point: 374.849oC at 760 mmHg
• Flash Point: 174.346oC
• PSA: 114.43000
• Density: 1.308g/cm3
• LogP: 0.03900
• Storage Temp.: −20°C
• Solubility.: soluble in Chloroform
• 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%, ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-a-D-glucopyranosyl fluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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-glucopyranosyl Fluoride

There total 87 articles about 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl 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:

α,β-Trehaloseoctaacetat

β-D-glucopyranosyl fluoride

1-deoxy-1-fluoro-α-D-glucose

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Refernces

• 1、 See, Nicholas W.,Wimmer, Norbert,Krenske, Elizabeth H.,Ferro, Vito. "A Substituent-Directed Strategy for the Selective Synthesis of L-Hexoses: An Expeditious Route to L-Idose". . p. 1575 - 1584. Retrieved 2021/03/03.
• 2、 Bachmann, Thomas,Rychlik, Michael. "Chemical glucosylation of pyridoxine". . . Retrieved 2020/02/13.