(2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran

Base Information

Chemical Name:(2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran
CAS No.:1330578-73-8
Molecular Formula:C₁₇H₁₉N₃O₃
Molecular Weight:313.356
Hs Code.:

Synonyms:(2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran

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Chemical Property of (2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran

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Technology Process of (2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran

There total 7 articles about (2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran 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%

: 1255790-37-4
(1R,3R,4S,5R)-3-azido-1-(furan-1'-yl)-tetrahydro-5-methyl-2H-pyran-4-ol

: 100-39-0
benzyl bromide

: 1330578-73-8
(2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tet.2011.05.117

Reference yield:

: 1330579-15-1
C₁₂H₁₅N₃O₄

: 1330578-73-8
(2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: methanol; potassium carbonate / 20 h / 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

With methanol; sodium hydride; potassium carbonate; In N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2011.05.117

Reference yield:

: 127112-84-9,127112-87-2,132814-68-7,132814-74-5
3,4-di-O-acetyl-2,6-dideoxy-α,β-D-arabino-hexopyranose

: 1330578-73-8
(2R,4R,5S,6R)-4-azido-5-benzyloxy-2-(furan-2-yl)-6-methyltetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: sodium azide; acetic acid / Inert atmosphere

2: pyridine; dmap / dichloromethane / Inert atmosphere

3: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

4: methanol; potassium carbonate / 20 h / 20 °C / Inert atmosphere

5: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; methanol; dmap; sodium azide; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Friedel Crafts alkylation;
DOI:10.1016/j.tet.2011.05.117