(R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate

Base Information

Chemical Name:(R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate
CAS No.:1403588-91-9
Molecular Formula:C₃₈H₄₁N₃O₇
Molecular Weight:651.759
Hs Code.:

Synonyms:(R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate

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Chemical Property of (R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate

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Technology Process of (R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate

There total 9 articles about (R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate 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: 80.0%

: (R)-methyl 2-azido-3-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)propanoate

: 1403588-91-9
(R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - -50 ℃; for 4.33333h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/ijch.201500087

Reference yield:

: 67-56-1
methanol

: C₃₇H₃₉N₃O₇

: 1403588-91-9
(R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate

Guidance literature:: With thionyl chloride; In acetone; at 0 - 20 ℃; for 1.58333h; Inert atmosphere;
DOI:10.1039/c2ob26078f

Reference yield:

: C₃₇H₄₂O₇

: 1403588-91-9
(R)-methyl 2-azido-3-((2S,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-propanoate

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / 24 h / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 7 h / 120 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C / Inert atmosphere

5: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; trichloroisocyanuric acid / acetone / 1.08 h / 0 °C / Inert atmosphere

6: thionyl chloride / acetone / 1.58 h / 0 - 20 °C / Inert atmosphere

With pyridine; thionyl chloride; sodium azide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; sodium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/c2ob26078f