methyl 3-{4-[4-(3-pyridinyl)-1-imidazolyl]butylamino}-4-O-p-methoxybenzyl-6-C-methyl-2,3,6-trideoxy-α-D-ribo-hexopyranoside

Base Information

Chemical Name:methyl 3-{4-[4-(3-pyridinyl)-1-imidazolyl]butylamino}-4-O-p-methoxybenzyl-6-C-methyl-2,3,6-trideoxy-α-D-ribo-hexopyranoside
CAS No.:872182-91-7
Molecular Formula:C₂₈H₃₈N₄O₄
Molecular Weight:494.634
Hs Code.:

Synonyms:

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Chemical Property of methyl 3-{4-[4-(3-pyridinyl)-1-imidazolyl]butylamino}-4-O-p-methoxybenzyl-6-C-methyl-2,3,6-trideoxy-α-D-ribo-hexopyranoside

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Technology Process of methyl 3-{4-[4-(3-pyridinyl)-1-imidazolyl]butylamino}-4-O-p-methoxybenzyl-6-C-methyl-2,3,6-trideoxy-α-D-ribo-hexopyranoside

There total 12 articles about methyl 3-{4-[4-(3-pyridinyl)-1-imidazolyl]butylamino}-4-O-p-methoxybenzyl-6-C-methyl-2,3,6-trideoxy-α-D-ribo-hexopyranoside 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:

: 872182-82-6
methyl 4-O-benzyl-2,6-dideoxy-6-C-methyl-α-D-arabino-hexopyranoside

: 872182-91-7
methyl 3-{4-[4-(3-pyridinyl)-1-imidazolyl]butylamino}-4-O-p-methoxybenzyl-6-C-methyl-2,3,6-trideoxy-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / pyridine / 12 h / 0 - 20 °C

2: 93 percent / hydrogen / palladium on carbon / ethyl acetate / 10 h

3: 76 percent / sodium azide / dimethylformamide / 12 h / 125 °C

4: 94 percent / sodium hydride / dimethylformamide; toluene / 6 h / 0 - 20 °C

5: trimethylphosphine / tetrahydrofuran; toluene; H₂O / 0.75 h / Heating

6: sodium cyanoborohydride; acetic acid / methanol / 12 h / 20 °C

With pyridine; sodium azide; hydrogen; sodium hydride; sodium cyanoborohydride; acetic acid; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 5: Staudinger reduction;
DOI:10.1139/v05-095

Reference yield:

: 872182-68-8
methyl 4-O-benzyl-2,6-dideoxy-6-C-methyl-α-D-ribo-hexopyranoside

: 872182-91-7
methyl 3-{4-[4-(3-pyridinyl)-1-imidazolyl]butylamino}-4-O-p-methoxybenzyl-6-C-methyl-2,3,6-trideoxy-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C

2: 93 percent / sodium methoxide; methanol / 10 h / 20 °C

3: 97 percent / pyridine / 12 h / 0 - 20 °C

4: 93 percent / hydrogen / palladium on carbon / ethyl acetate / 10 h

5: 76 percent / sodium azide / dimethylformamide / 12 h / 125 °C

6: 94 percent / sodium hydride / dimethylformamide; toluene / 6 h / 0 - 20 °C

7: trimethylphosphine / tetrahydrofuran; toluene; H₂O / 0.75 h / Heating

8: sodium cyanoborohydride; acetic acid / methanol / 12 h / 20 °C

With pyridine; methanol; sodium azide; di-isopropyl azodicarboxylate; hydrogen; sodium methylate; sodium hydride; sodium cyanoborohydride; acetic acid; triphenylphosphine; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Mitsunobu reaction / 7: Staudinger reduction;
DOI:10.1139/v05-095

Reference yield:

: 872182-66-6
methyl 4-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside

: 872182-91-7
methyl 3-{4-[4-(3-pyridinyl)-1-imidazolyl]butylamino}-4-O-p-methoxybenzyl-6-C-methyl-2,3,6-trideoxy-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: 80 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

2.1: copper(I) iodide / diethyl ether / 0.33 h / -5 °C

2.2: 89 percent / diethyl ether / 4 h / -78 - 20 °C

3.1: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C

4.1: 93 percent / sodium methoxide; methanol / 10 h / 20 °C

5.1: 97 percent / pyridine / 12 h / 0 - 20 °C

6.1: 93 percent / hydrogen / palladium on carbon / ethyl acetate / 10 h

7.1: 76 percent / sodium azide / dimethylformamide / 12 h / 125 °C

8.1: 94 percent / sodium hydride / dimethylformamide; toluene / 6 h / 0 - 20 °C

9.1: trimethylphosphine / tetrahydrofuran; toluene; H₂O / 0.75 h / Heating

10.1: sodium cyanoborohydride; acetic acid / methanol / 12 h / 20 °C

With pyridine; methanol; copper(l) iodide; sodium azide; di-isopropyl azodicarboxylate; hydrogen; sodium methylate; sodium hydride; sodium cyanoborohydride; acetic acid; triphenylphosphine; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 3.1: Mitsunobu reaction / 9.1: Staudinger reduction;
DOI:10.1139/v05-095