1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene

Base Information

• Chemical Name: 1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene
• CAS No.: 767340-72-7
• Molecular Formula: C₃₂H₃₆O₇
• Molecular Weight: 532.634
• Mol file: 767340-72-7.mol

Synonyms:1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene

Chemical Property of 1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene

There total 4 articles about 1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene 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: 70.0%

2-O-acetyl-3,4,6-tri-O-benzyl-D-mannono-1,5-lactone (651718-17-1) + allylmagnesium bromide (1730-25-2) → 1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene (767340-72-7)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h;

DOI:10.1021/jo049061w

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) → 1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene (767340-72-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: K₂CO₃ / methanol / 2 h / 20 °C

2.1: NaH / dimethylformamide / 1 h / 0 °C

2.2: dimethylformamide / 24 h / 20 °C

3.1: H₂O / 0.33 h / 20 °C

3.2: 90 percent / NMO; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / acetonitrile / 0.08 h / 20 °C

4.1: 70 percent / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

With sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1021/jo049061w

Reference yield:

1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (29073-91-4,55865-04-8,138196-19-7) → 1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene (767340-72-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 1 h / 0 °C

1.2: dimethylformamide / 24 h / 20 °C

2.1: H₂O / 0.33 h / 20 °C

2.2: 90 percent / NMO; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / acetonitrile / 0.08 h / 20 °C

3.1: 70 percent / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

With sodium hydride; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1021/jo049061w

upstream raw materials:

2-O-acetyl-3,4,6-tri-O-benzyl-D-mannono-1,5-lactone

allylmagnesium bromide

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Downstream raw materials:

1-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)prop-2-ene

1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)prop-2-ene