(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol
CAS No.:850004-57-8
Molecular Formula:C₂₆H₃₇NO₇Si
Molecular Weight:503.668
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol

There total 9 articles about (2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol 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%

: 850004-56-7
2-nitrobenzyl 3-O-benzyl-β-D-fucopyranoside

: 18162-48-6
tert-butyldimethylsilyl chloride

: 850004-57-8
(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 23 ℃; for 12.25h;
DOI:10.1021/ja0422007

Reference yield:

: 132938-42-2
(2R,3R,4S,5R,6R)-2-Methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3,4,5-triol

: 850004-57-8
(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 40 percent / Bu₂SnO; tetrabutylammonium bromide / toluene / 36.5 h / Heating

2: 96 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 12.25 h / 20 °C

With 1H-imidazole; dmap; tetrabutylammomium bromide; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja062364i

Reference yield:

: 73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6
D-Fucose

: 850004-57-8
(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / triethylamine / CH₂Cl₂

2: HBr; acetic acid / CH₂Cl₂

3: Ag₂O / CH₂Cl₂

4: 90 percent / potassium carbonate / methanol

5: 40 percent / Bu₂SnO; tetrabutylammonium bromide / toluene / 36.5 h / Heating

6: 96 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 12.25 h / 20 °C

With 1H-imidazole; dmap; tetrabutylammomium bromide; hydrogen bromide; di(n-butyl)tin oxide; potassium carbonate; acetic acid; triethylamine; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja062364i