(2S,3R,4R,5S,6R)-5-Fluoro-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diol

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-5-Fluoro-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diol
• CAS No.: 56926-53-5
• Molecular Formula: C7H13FO5
• Molecular Weight: 196.17
• UNII: CBN7HL3RFS
• Mol file: 56926-53-5.mol

Synonyms:56926-53-5;CBN7HL3RFS;Methyl 4-Deoxy-4-fluoro-alpha-D-glucose;UNII-CBN7HL3RFS;(2S,3R,4R,5S,6R)-5-Fluoro-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diol;alpha-Methyl-4-deoxy-4-fluoro-D-glucopyranoside;(2S,3R,4R,5S,6R)-5-FLUORO-6-(HYDROXYMETHYL)-2-METHOXYOXANE-3,4-DIOL;methyl 4-deoxy-4-fluoro-alpha-d-glucopyranoside;alpha-D-Glucopyranoside, methyl 4-deoxy-4-fluoro-;.alpha.-D-Glucopyranoside, methyl 4-deoxy-4-fluoro-;METHYL 4-DEOXY-4-FLUORO-ALPHA-D-GLUCOSIDE;Methyl 4-deoxy-4-fluoro-a-D-glucose;SCHEMBL3163690;AKOS006286778;Methyl 4-Deoxy-4-fluoro-?-D-glucose;Methyl 4-Deoxy-4-fluoro- alpha -D-glucose;W-203146;METHYL 4-DEOXY-4-FLUORO-.ALPHA.-D-GLUCOPYRANOSIDE

Chemical Property of (2S,3R,4R,5S,6R)-5-Fluoro-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 125-127°C
• Refractive Index: 1.492
• Boiling Point: 352.717°C at 760 mmHg
• Flash Point: 163.456°C
• PSA: 79.15000
• Density: 1.406g/cm³
• LogP: -1.59010
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Very Slightly), Water (Slightly, Sonicated)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 196.07470167
• Heavy Atom Count: 13
• Complexity: 167

Purity/Quality:

≥95% ^*data from raw suppliers

Methyl 4-deoxy-4-fluoro-a-D-glucose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)CO)F)O)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)F)O)O
• Uses: Methyl 4-Deoxy-4-fluoro-α-D-glucose (cas# 56926-53-5) is a compound useful in organic synthesis.

Technology Process of (2S,3R,4R,5S,6R)-5-Fluoro-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diol

There total 4 articles about (2S,3R,4R,5S,6R)-5-Fluoro-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diol 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: 78.0%

methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-α-D-glucopyranoside (51996-36-2,84065-98-5,141990-21-8) → Methyl 4-Deoxy-4-fluoro-α-D-glucopyranoside (56926-53-5)

Guidance literature:

With sodium methylate; for 18h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90028-4

Reference yield: 77.0%

Methyl 2,3,6-Tri-O-benzoyl-4-deoxy-4-fluoro-α-D-glucopyranoside (84065-98-5) → Methyl 4-Deoxy-4-fluoro-α-D-glucopyranoside (56926-53-5)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1016/0008-6215(87)80239-2

Reference yield:

methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside (3601-36-3,6344-46-3) → Methyl 4-Deoxy-4-fluoro-α-D-glucopyranoside (56926-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 50.5 percent / DAST / CH₂Cl₂

2: 65.9 percent / NaOMe / methanol

With sodium methylate; 4,4'-diaminostilbene-2,2'-disulfonic acid; In methanol; dichloromethane;

DOI:10.1021/jo00102a024

upstream raw materials:

Methyl 2,3,6-Tri-O-benzoyl-4-deoxy-4-fluoro-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside

Downstream raw materials:

4-deoxy-4-fluoro-β-D-glucopyranose

3-fluoro-3-deoxy-α-D-glucose

(3R,4R,5S,6R)-5-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol

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