3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose

Base Information

Chemical Name:3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose
CAS No.:161045-48-3
Molecular Formula:C₁₉H₂₅N₃O₅
Molecular Weight:375.425
Hs Code.:

Synonyms:3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose

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Chemical Property of 3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose

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Technology Process of 3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose

There total 6 articles about 3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 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:

: 20316-77-2
(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

: 161045-48-3
3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: 175 g / acetic acid; H₂O / 16 h / 60 °C

2.1: CH₂Cl₂; pyridine / 1 h / -15 °C

3.1: 179 g / CH₂Cl₂; pyridine / 20 h / -15 - 20 °C

4.1: NaOMe / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

4.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C

5.1: 3.70 g / NH₄Cl; NaN₃ / dimethylformamide; H₂O / 2 h / 80 °C

6.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C

With sodium azide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00642-1

Reference yield:

: 91882-92-7
3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

: 161045-48-3
3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: CH₂Cl₂; pyridine / 1 h / -15 °C

2.1: 179 g / CH₂Cl₂; pyridine / 20 h / -15 - 20 °C

3.1: NaOMe / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

3.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C

4.1: 3.70 g / NH₄Cl; NaN₃ / dimethylformamide; H₂O / 2 h / 80 °C

5.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C

With sodium azide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00642-1

Reference yield:

: Benzoic acid (R)-2-((3aR,5R,6S,6aR)-6-allyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester

: 161045-48-3
3-O-allyl-6-azido-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 179 g / CH₂Cl₂; pyridine / 20 h / -15 - 20 °C

2.1: NaOMe / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

2.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C

3.1: 3.70 g / NH₄Cl; NaN₃ / dimethylformamide; H₂O / 2 h / 80 °C

4.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C

With sodium azide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00642-1