2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose

Base Information

• Chemical Name: 2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose
• CAS No.: 80779-87-9
• Molecular Formula: C20H27O10
• Molecular Weight: 438.431
• Mol file: 80779-87-9.mol

Synonyms:1,3,4,6-Tetra-O-acetyl-2-O-benzyl-a-D-mannopyranose;1,3,4,6-Tetra-O-acetyl-2-O-benzyl-α-D-Mannopyranose;2-O-(PhenylMethyl)-α-D-Mannopyranose 1,3,4,6-Tetraacetate

Chemical Property of 2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 65-70°C
• Boiling Point: 514.203°C at 760 mmHg
• Flash Point: 221.178°C
• PSA: 123.66000
• Density: 1.276g/cm³
• LogP: 1.28630
• Storage Temp.: -20°C Freezer

Purity/Quality:

99.3% ^*data from raw suppliers

1,3,4,6-Tetra-O-acetyl-2-O-benzyl-a-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose is Used for the preparation of the corresponding bromide, to be used as an agent for the preparation of -mannosides.

Technology Process of 2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose

There total 6 articles about 2-O-Benzyl-1,3,4,6-tetra-O-acetyl-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: 80.0%

acetic anhydride (108-24-7) + methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside (15038-71-8,15384-58-4,23392-29-2,40653-23-4,57539-07-8,76375-66-1,81872-62-0,86363-45-3,90639-38-6,108739-91-9,116002-34-7,130192-76-6,131433-04-0,141115-75-5,78185-83-8) → 1,3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-mannopyranoside (80779-87-9)

Guidance literature:

With sulfuric acid; at 25 ℃; for 0.666667h;

Reference yield: 80.0%

O2-benzyl-O3,O4-isopropyliden-1,6-anhydro-β-D-galactopyranose (55287-62-2) + acetic anhydride (108-24-7) → 1,3,4,6-Tetra-O-acetyl-2-O-benzyl-D-galactopyranose (29741-67-1,30253-76-0,53872-77-8,72984-63-5,79733-81-6,80779-87-9,95403-48-8)

Guidance literature:

With trifluoroacetic acid; at 0 - 20 ℃;

DOI:10.1021/ja045385q

Reference yield:

benzyl bromide (100-39-0) → 1,3,4,6-Tetra-O-acetyl-2-O-benzyl-D-galactopyranose (29741-67-1,30253-76-0,53872-77-8,72984-63-5,79733-81-6,80779-87-9,95403-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 20 °C

2: 80 percent / trifluoroacetic acid / 0 - 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/ja045385q

upstream raw materials:

O²-benzyl-O³,O⁴-isopropyliden-1,6-anhydro-β-D-galactopyranose

acetic anhydride

benzyl bromide

1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose

Downstream raw materials:

Benzyl-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid

Benzyl-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid

(2,2,2-Trichlorethyl)-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid

Benzyl-4-0-(2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid

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