5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose

Base Information

Chemical Name:5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose
CAS No.:912943-03-4
Molecular Formula:C₁₇H₂₃N₃O₅
Molecular Weight:349.387
Hs Code.:

Synonyms:5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose

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Chemical Property of 5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose

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Technology Process of 5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose

There total 7 articles about 5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose 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: 100.0%

: 912943-01-2
5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-7-O-triisopropylsilyl-β-L-talo-hepto-1,4-furanose

: 912943-03-4
5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;
DOI:10.1016/j.tetasy.2006.07.022

Reference yield:

: 912942-95-1
3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-allo-hepto-1,4-furanose

: 912943-03-4
5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / imidazole / dimethylformamide / 1 h / 20 °C

2: 73 percent / pyridine / CH₂Cl₂ / 1.5 h / 45 °C

3: 76 percent / sodium azide / dimethylformamide / 3 h / 110 °C

4: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

With pyridine; 1H-imidazole; sodium azide; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2006.07.022

Reference yield:

: 912942-93-9
methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-oxo-α-D-ribo-heptofuranuronate

: 912943-03-4
5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / [((S)-Binap)RuBr₂]; hydrogen / methanol / 24 h / 45 °C / 760 Torr

2: 78 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

3: 85 percent / imidazole / dimethylformamide / 1 h / 20 °C

4: 73 percent / pyridine / CH₂Cl₂ / 1.5 h / 45 °C

5: 76 percent / sodium azide / dimethylformamide / 3 h / 110 °C

6: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; sodium azide; (S)-BinapRuBr₂; tetrabutyl ammonium fluoride; hydrogen; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2006.07.022