Glucosyl fluoride

Base Information

• Chemical Name: Glucosyl fluoride
• CAS No.: 2106-10-7
• Molecular Formula: C6H11FO5
• Molecular Weight: 182.149
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID30943370
• Mol file: 2106-10-7.mol

Synonyms:alpha-D-glucopyranosyl fluoride;beta-D-glucopyranosyl fluoride;glucosyl fluoride;glucosyl fluoride, (beta-D)-isomer

Chemical Property of Glucosyl fluoride

Chemical Property:

• Vapor Pressure: 4.99E-07mmHg at 25°C
• Melting Point: 190-200 °C (decomp)
• Boiling Point: 371.3°Cat760mmHg
• PKA: 12.40±0.70(Predicted)
• Flash Point: 170.6°C
• PSA: 90.15000
• Density: 1.59g/cm³
• LogP: -2.24420
• Storage Temp.: ?20°C
• 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:

99%, ^*data from raw suppliers

α-D-GlucopyranosylFluoride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

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(O1)F)O)O)O)O
• Uses: Alpha-D-glucopyranosyl fluoride

Technology Process of Glucosyl fluoride

There total 12 articles about Glucosyl 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: 100.0%

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) → 1-deoxy-1-fluoro-α-D-glucose (2106-10-7)

Guidance literature:

With methanol; sodium methylate; at 0 ℃; for 2h; pH=8.5;

DOI:10.1021/ma100191d

Reference yield:

D-Glucose (2280-44-6) → 1-thio-α,α-trehalose (17317-98-5,18977-84-9,68667-06-1,68778-86-9,68778-87-0,68778-88-1,108392-13-8,62853-32-1,80441-61-8) + 1-thio-β-D-glucopyranose (22566-82-1,23558-19-2,49858-49-3,63073-99-4,135891-42-8,7534-35-2) + (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triol (63073-99-4) + 1-deoxy-1-fluoro-α-D-glucose (2106-10-7)

Guidance literature:

With hydrogen sulfide; In hydrogen fluoride; at -10 ℃; for 1h; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0008-6215(91)84116-V

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;

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:

methyl-alpha-D-glucopyranoside

methyl beta-D-glucopyranoside

levoglucosan

2,3,4-tri-O-acetyllevoglucosan

Refernces

• 1、 Defaye, Jacques,Gadelle, Andree. "THE BEHAVIOR OF CELLULOSE, AMYLOSE, AND β-D-XYLAN TOWARDS ANHYDROUS HYDROGEN FLUORIDE". . p. 217 - 228. Retrieved 1982.
• 2、 Zhang, Jianbo,Park, Sehoon,Chang, Sukbok. "Selective C?O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ". supporting information. p. 13757 - 13761. Retrieved 2017/10/09.
• 3、 Pozzo, Tania,Plaza, Merichel,Romero-Garcia, Javier,Faijes, Magda,Karlsson, Eva Nordberg,Planas, Antoni. "Glycosynthases from Thermotoga neapolitana β-glucosidase 1A: A comparison of α-glucosyl fluoride and in situ-generated α-glycosyl formate donors". . p. 132 - 139. Retrieved 2014/07/21.