3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

Base Information

Chemical Name:3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose
CAS No.:270087-60-0
Molecular Formula:C₂₉H₄₂O₇Si
Molecular Weight:530.734
Hs Code.:

Synonyms:3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

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Chemical Property of 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

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Technology Process of 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

There total 9 articles about 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-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: 46.0%

: 100-39-0
benzyl bromide

: (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

: 270087-60-0
3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

Guidance literature:: (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1039/d0cc05573e

Reference yield:

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

: 270087-60-0
3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / tetrahydrofuran / 3 h

2: 3.29 g / NaH; TBAI / dimethylformamide / 0 - 20 °C

With 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300483

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

: 270087-60-0
3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

Guidance literature:: Multi-step reaction with 3 steps

1: K₂CO₃ / methanol / 6 h / 20 °C

2: imidazole / dimethylformamide / 5 h / 20 °C

3: 412.1 mg / tetrabutylammonium iodide; NaH / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja028386w