((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Base Information

Chemical Name:((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester
CAS No.:725740-19-2
Molecular Formula:C₂₀H₂₂N₄O₆
Molecular Weight:414.418
Hs Code.:

Synonyms:((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

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Chemical Property of ((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

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Technology Process of ((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

There total 12 articles about ((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 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: 99.0%

: 884525-59-1
Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-azidomethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester

: 725740-19-2
((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Guidance literature:: With methanol; triethylamine; at 50 ℃; for 2h;
DOI:10.1021/ja056253f

Reference yield:

: 122210-05-3
1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose

: 725740-19-2
((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / SnCl₄ / CH₂Cl₂ / 48 h / 20 °C

2: Zn; AcOH / tetrahydrofuran / 1.5 h / 20 °C

3: 1.13 g / aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

4: Et₃N; MeOH / 12 h / 20 °C

5: pyridine / 1.5 h / 20 °C

6: 120 mg / pyridine / 1.5 h / 20 °C

7: 89 percent / NaN₃ / dimethylformamide / 2 h / 80 °C

8: 99 percent / Et₃N; MeOH / 2 h / 50 °C

With pyridine; methanol; sodium azide; tin(IV) chloride; sodium hydrogencarbonate; acetic acid; triethylamine; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja056253f

Reference yield:

: ((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

: 725740-19-2
((2R,3R,4R,5S,6R)-6-Azidomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 1.5 h / 20 °C

2: 120 mg / pyridine / 1.5 h / 20 °C

3: 89 percent / NaN₃ / dimethylformamide / 2 h / 80 °C

4: 99 percent / Et₃N; MeOH / 2 h / 50 °C

With pyridine; methanol; sodium azide; triethylamine; In N,N-dimethyl-formamide;
DOI:10.1021/ja056253f