N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

Base Information

Chemical Name:N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride
CAS No.:637330-41-7
Molecular Formula:C₄₄H₇₂ClN₃O₁₂Si₃
Molecular Weight:954.778
Hs Code.:

N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

Synonyms:N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

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Chemical Property of N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

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Technology Process of N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

There total 10 articles about N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride 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:

: 75-44-5
phosgene

: N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine hydrochloride

: 637330-41-7
N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

Guidance literature:: With triethylamine; In toluene; at 0 ℃; for 2.5h;
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

: 637330-41-7
N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

Guidance literature:: Multi-step reaction with 10 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

7: 54 percent / pyridine / CH₂Cl₂ / 20 °C

8: 38 mg / pyridine / CH₂Cl₂ / 5 h / 20 °C

9: aq. HCl / ethyl acetate / 0 °C

10: 230 mg / Et₃N / toluene / 2.5 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; titanium(IV) tetraethanolate; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; silica gel; acetic acid; triethylamine; In pyridine; methanol; dichloromethane; chloroform; ethyl acetate; 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

: 637330-41-7
N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

Guidance literature:: Multi-step reaction with 9 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

6: 54 percent / pyridine / CH₂Cl₂ / 20 °C

7: 38 mg / pyridine / CH₂Cl₂ / 5 h / 20 °C

8: aq. HCl / ethyl acetate / 0 °C

9: 230 mg / Et₃N / toluene / 2.5 h / 0 °C

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