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
Hs Code.:

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

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

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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%

: 651718-17-1
2-O-acetyl-3,4,6-tri-O-benzyl-D-mannono-1,5-lactone

: 1730-25-2
allylmagnesium bromide

: 767340-72-7
1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h;
DOI:10.1021/jo049061w

Reference yield:

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

: 767340-72-7
1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene

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:

: 29073-91-4,55865-04-8,138196-19-7
1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

: 767340-72-7
1-(2'-O-acetyl-3',4',6'-tri-O-benzyl-1'-hydroxy-α-D-mannonopyranosyl)prop-2-ene

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