beta-D-Galactopyranosyl fluoride

Base Information

• Chemical Name: beta-D-Galactopyranosyl fluoride
• CAS No.: 2021-62-7
• Molecular Formula: C₆H₁₁FO₅
• Molecular Weight: 182.149
• DSSTox Substance ID: DTXSID801307516
• Nikkaji Number: J1.420.799F
• Mol file: 2021-62-7.mol

Synonyms:beta-D-Galactopyranosyl fluoride;2021-62-7;beta-galactosyl fluoride;SCHEMBL8992769;DTXSID801307516

Chemical Property of beta-D-Galactopyranosyl fluoride

Chemical Property:

• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 182.05905161
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)F)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)F)O)O)O)O

Technology Process of beta-D-Galactopyranosyl fluoride

There total 4 articles about beta-D-Galactopyranosyl 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:

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) → β-D-glucopyranosyl fluoride (447-27-8,447-29-0,2021-62-7,2021-84-3,2106-10-7,2713-54-4,7617-95-0,80409-18-3,80409-19-4)

Guidance literature:

With methanol; sodium methylate;

Reference yield:

2-O-methanesulfonyl-β-D-mannose (221252-44-4) → β-D-glucopyranosyl fluoride (447-27-8,447-29-0,2021-62-7,2021-84-3,2106-10-7,2713-54-4,7617-95-0,80409-18-3,80409-19-4)

Guidance literature:

With tetraethylammonium fluoride; In tetrahydrofuran; acetonitrile; at 20 ℃;

DOI:10.1002/(SICI)1099-1344(199902)42:2<147::AID-JLCR176>3.0.CO;2-E

Reference yield:

1,3,4,6-tetra-O-acetyl-2-O-methanesulfonyl-β-D-mannose (221252-41-1) → β-D-glucopyranosyl fluoride (447-27-8,447-29-0,2021-62-7,2021-84-3,2106-10-7,2713-54-4,7617-95-0,80409-18-3,80409-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / aq. HCl / 0.5 h / Heating

2: 500 mg / tetraethylammonium fluoride dihydrate / acetonitrile; tetrahydrofuran / 20 °C

With hydrogenchloride; tetraethylammonium fluoride; In tetrahydrofuran; acetonitrile; 1: Deacetylation / 2: Substitution;

DOI:10.1002/(SICI)1099-1344(199902)42:2<147::AID-JLCR176>3.0.CO;2-E

upstream raw materials:

2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate

2-O-methanesulfonyl-β-D-mannose

1,3,4,6-tetra-O-acetyl-2-O-methanesulfonyl-β-D-mannose

1,3,4,6-tetra-O-acetyl-β-D-mannopyranose

Downstream raw materials:

O⁶-trityl-β-D-glucopyranosyl fluoride

O⁴,O⁶-((R)-benzylidene)-β-D-glucopyranosyl fluoride

levoglucosan

2,3,4-tri-O-acetyllevoglucosan

Refernces

• 1、 De Groot, Tjibbe,Bormans, Guy,Busson, Roger,Mortelmans, Luc,Verbruggen, Alfons. "Synthesis of 1-[18F]fluorodeoxyglucose: An unexpected rearrangement in the reaction of 2-O-methanesulfonyl-β-D-mannopyranose with [18F]fluoride". . p. 147 - 157. Retrieved 2007/10/03.