1,2,4,6-Tetra-O-acetyl-3-O-benzyl-a-D-mannopyranose

Base Information

• Chemical Name: 1,2,4,6-Tetra-O-acetyl-3-O-benzyl-a-D-mannopyranose
• CAS No.: 65827-58-9
• Molecular Formula: C20H27O10
• Molecular Weight: 438.431
• DSSTox Substance ID: DTXSID20553402
• Wikidata: Q82433979
• Mol file: 65827-58-9.mol

Synonyms:65827-58-9;1,2,4,6-Tetra-O-acetyl-3-O-benzyl-a-D-mannopyranose;3-O-Benzyl-1,2,4,6-tetra-O-acetyl-a-D-mannopyranose;[(2R,3R,4S,5S,6R)-3,5,6-triacetyloxy-4-phenylmethoxyoxan-2-yl]methyl acetate;SCHEMBL17502040;DTXSID20553402;W-203438;1,2,4,6-Tetra-O-acetyl-3-O-benzyl-alpha-D-mannopyranose;3-O-Benzyl-1,2,4,6-tetra-O-acetyl- alpha -D-mannopyranose;3-O-BENZYL-1,2,4,6-TETRA-O-ACETYL-alpha-D-MANNOPYRANOSE

Chemical Property of 1,2,4,6-Tetra-O-acetyl-3-O-benzyl-a-D-mannopyranose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 514.203°C at 760 mmHg
• Flash Point: 221.178°C
• PSA: 123.66000
• Density: 1.276g/cm³
• LogP: 1.28630
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 438.15259702
• Heavy Atom Count: 31
• Complexity: 642

Purity/Quality:

98%min ^*data from raw suppliers

3-O-Benzyl-1,2,4,6-tetra-O-acetyl-α-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OCC2=CC=CC=C2)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC(=O)C)OC(=O)C)OCC2=CC=CC=C2)OC(=O)C

Technology Process of 1,2,4,6-Tetra-O-acetyl-3-O-benzyl-a-D-mannopyranose

There total 43 articles about 1,2,4,6-Tetra-O-acetyl-3-O-benzyl-a-D-mannopyranose 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: 96.0%

acetic anhydride (108-24-7) + methyl 3-O-benzyl-α-D-mannopyranoside (93714-01-3) → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-mannopyranoside (65827-58-9)

Guidance literature:

With sulfuric acid; at 20 ℃; for 3h; Schlenk technique;

DOI:10.1039/c8nj06191b

Reference yield: 91.0%

acetic anhydride (108-24-7) + (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,94062-87-0,108739-92-0,129706-93-0,143005-12-3,65877-21-6) → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-mannopyranoside (65827-58-9)

Guidance literature:

With sulfuric acid; at 25 ℃; for 0.333333h;

Reference yield: 90.0%

3-O-benzyl-D-glucopyranose (65877-63-6,97590-76-6,99396-09-5,5531-09-9) + acetic anhydride (108-24-7) → 3-O-benzyl-1,2,4,6-tetra-O-acetyl-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9)

Guidance literature:

With pyridine; at 20 ℃; for 8h;

DOI:10.1016/j.tet.2018.03.057

upstream raw materials:

O³-benzyl-D-glucose

acetic anhydride

3-O-benzyl-D-glucopyranose

benzyl-O-β-D-glucopyranoside

Downstream raw materials:

methyl-(O³-benzyl-O²,O⁴,O⁶-trimethyl-ξ-D-glucopyranoside)

benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside

1-O-Acetyl-3-O-benzyl-2,4,6-tri-O-methyl-β-D-glucopyranose

1-O-Acetyl-3-O-benzyl-2,4,6-tri-O-methyl-α-D-glucopyranose