[(2S,3R,4S,5R)-4,5,6-Triacetyloxy-2-(fluoromethyl)oxan-3-yl] acetate

Base Information

• Chemical Name: [(2S,3R,4S,5R)-4,5,6-Triacetyloxy-2-(fluoromethyl)oxan-3-yl] acetate
• CAS No.: 155488-15-6
• Molecular Formula: C14H19 F O9
• Molecular Weight: 350.29
• DSSTox Substance ID: DTXSID10455986
• Mol file: 155488-15-6.mol

Synonyms:155488-15-6;[(2S,3R,4S,5R)-4,5,6-Triacetyloxy-2-(fluoromethyl)oxan-3-yl] acetate;1,2,3,4-TETRA-O-ACETYL-6-DEOXY-6-FLUORO-D-GALACTOPYRANOSE;CTK4C8712;DTXSID10455986;NGYYXVXMDLMRLI-RRYROLNDSA-N

Chemical Property of [(2S,3R,4S,5R)-4,5,6-Triacetyloxy-2-(fluoromethyl)oxan-3-yl] acetate

Chemical Property:

• Boiling Point: 387.8±42.0 °C(Predicted)
• PSA: 114.43000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 0.03900
• 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:

97% ^*data from raw suppliers

1,2,3,4-TETRA-O-ACETYL-6-DEOXY-6-FLUORO-D-GALACTOPYRANOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(OC(C(C1OC(=O)C)OC(=O)C)OC(=O)C)CF
• Isomeric SMILES: CC(=O)O[C@H]1[C@H](OC([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)CF

Technology Process of [(2S,3R,4S,5R)-4,5,6-Triacetyloxy-2-(fluoromethyl)oxan-3-yl] acetate

There total 4 articles about [(2S,3R,4S,5R)-4,5,6-Triacetyloxy-2-(fluoromethyl)oxan-3-yl] acetate 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: 95.0%

6-deoxy-6-fluoro-D-galactopyranose (447-25-6,34168-77-9,62182-12-1,62182-13-2,143616-86-8,18961-68-7,502642-85-5) + acetic anhydride (108-24-7) → 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-D-galactopyranose (155488-15-6,674782-58-2)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 12h;

Reference yield:

6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose (2021-97-8,6185-32-6,70981-54-3) + acetic anhydride (108-24-7) → 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-D-galactopyranose (155488-15-6,674782-58-2)

Guidance literature:

6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose; With acetic acid; In water; for 18h; Inert atmosphere; Reflux;

acetic anhydride; With pyridine; at 20 ℃; for 66h; Inert atmosphere;

DOI:10.1002/chem.201806197

Reference yield:

6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose (2021-97-8,6185-32-6,70981-54-3) → 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-D-galactopyranose (155488-15-6,674782-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃COOH, H₂O / CH₂Cl₂ / 1 h

2: pyridine

With pyridine; water; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/0008-6215(93)84068-H

upstream raw materials:

6-deoxy-6-fluoro-D-galactopyranose

acetic anhydride

6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Downstream raw materials:

N-[(2R,3R,4R,5S,6R)-2-(6-Azido-hexyloxy)-6-benzyloxymethyl-5-((2R,3R,4S,5R,6S)-6-fluoromethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

C₆₀H₇₅FN₄O₁₇

methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl)-β-D-glucopyranoside

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl)-β-D-glucopyranoside