benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate

Base Information

Chemical Name:benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate
CAS No.:637330-37-1
Molecular Formula:C₃₈H₆₃NO₁₀Si₃
Molecular Weight:778.175
Hs Code.:

Synonyms:benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate

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Chemical Property of benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate

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Technology Process of benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate

There total 6 articles about benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate 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: 85.0%

: 637330-36-0
benzyl {[2-nitro-4-(O-tert-butyldiphenylsilylmethyl)phenyl]-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid}uronate

: 637330-37-1
benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In N,N-dimethyl-formamide;
DOI:10.1039/b306236h

Reference yield:

: 148579-93-5
(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 637330-37-1
benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / NaBH₄; silica / CHCl₃; propan-2-ol / 0 - 20 °C

2: 65 percent / NaOMe / methanol / -15 - 20 °C

3: 85 percent / imidazole / dimethylformamide / 8 h / 20 °C

4: 84 percent / DMAP / pyridine; CH₂Cl₂ / 20 °C

5: 72 percent / Ti(OEt)4; 4 Angstroem molecular sieves / toluene / 48 h / Heating

6: 85 percent / AcOH; TBAF / dimethylformamide

With 1H-imidazole; dmap; titanium(IV) tetraethanolate; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; silica gel; acetic acid; In pyridine; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1039/b306236h

Reference yield:

: 148579-94-6
(25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 637330-37-1
benzyl [(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid]uronate

Guidance literature:: Multi-step reaction with 5 steps

1: 65 percent / NaOMe / methanol / -15 - 20 °C

2: 85 percent / imidazole / dimethylformamide / 8 h / 20 °C

3: 84 percent / DMAP / pyridine; CH₂Cl₂ / 20 °C

4: 72 percent / Ti(OEt)4; 4 Angstroem molecular sieves / toluene / 48 h / Heating

5: 85 percent / AcOH; TBAF / dimethylformamide

With 1H-imidazole; dmap; titanium(IV) tetraethanolate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/b306236h