2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl Fluoride

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl Fluoride
• CAS No.: 187269-63-2
• Molecular Formula: C26H43 F O9
• Molecular Weight: 518.61
• Hs Code.: 2932990090
• Mol file: 187269-63-2.mol

Synonyms:2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl Fluoride;SCHEMBL2592726;[(2R,3R,4S,5S,6R)-3,4,5-TRIS[(2,2-DIMETHYLPROPANOYL)OXY]-6-FLUOROOXAN-2-YL]METHYL 2,2-DIMETHYLPROPANOATE;[(2R,3R,4S,5S,6R)-3,4,5-TRIS[(2,2-DIMETHYLPROPANOYL)OXY]-6-FLUOROOXAN-2-YL]METHYL2,2-DIMETHYLPROPANOATE

Chemical Property of 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl Fluoride

Chemical Property:

• PSA: 114.43000
• LogP: 4.14380
• Storage Temp.: 0-10°C
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 13
• Exact Mass: 518.28911111
• Heavy Atom Count: 36
• Complexity: 824

Purity/Quality:

98% min ^*data from raw suppliers

2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl fluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OCC1C(C(C(C(O1)F)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• Isomeric SMILES: CC(C)(C)C(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)F)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• Uses: 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl fluoride (CAS# 187269-63-2) is a useful chiral building block used for stereospecific α-?D-?mannosylations. 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl fluoride also appears in the preparation of di- and trivalent phenyl substituted glycosides as selectin inhibitors.

Technology Process of 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl Fluoride

There total 4 articles about 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl 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: 80.0%

pivaloyl chloride (3282-30-2) + α-D-mannopyranosyl fluoride (2713-54-4) → 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl fluoride (187269-63-2)

Guidance literature:

With dmap; In pyridine; at 0 - 70 ℃;

DOI:10.1016/S0008-6215(99)00065-8

Reference yield:

penta-O-acetyl-D-mannose (66888-27-5) → 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl fluoride (187269-63-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / HF; pyridine / CH₂Cl₂ / 40 °C / sealed PFE flask

2: K₂CO₃ / methanol / 20 °C

3: 80 percent / 4-dimethylaminopyridine / pyridine / 0 - 70 °C

With pyridine; dmap; hydrogen fluoride; potassium carbonate; In pyridine; methanol; dichloromethane; 1: Fluorination / 2: Deacetylation / 3: Acylation;

DOI:10.1016/S0008-6215(99)00065-8

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride (2823-44-1,439-03-2,439-04-3,439-05-4,2823-46-3,3934-29-0,4163-44-4,4163-45-5,20409-31-8,23235-96-3,51897-75-7,51897-76-8,51897-77-9,57573-38-3,62561-28-8,126641-47-2) → 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl fluoride (187269-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / methanol / 20 °C

2: 80 percent / 4-dimethylaminopyridine / pyridine / 0 - 70 °C

With dmap; potassium carbonate; In pyridine; methanol; 1: Deacetylation / 2: Acylation;

DOI:10.1016/S0008-6215(99)00065-8

upstream raw materials:

pivaloyl chloride

α-D-mannopyranosyl fluoride

penta-O-acetyl-D-mannose

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride

Downstream raw materials:

4-nitrobenzyl tetra-O-pivaloyl-α-D-mannopyranoside

4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside

4-bromophenyl α-D-mannopyranoside

2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranose