(2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide

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Chemical Name:(2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide
CAS No.:688321-44-0
Molecular Formula:C₂₈H₃₈N₄O₆
Molecular Weight:526.633
Hs Code.:

Synonyms:(2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide

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Chemical Property of (2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide

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Technology Process of (2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide

There total 3 articles about (2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide 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: 64.0%

: 688321-43-9
(2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide

: 688321-44-0
(2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide

Guidance literature:: With trifluoroacetic acid; In dichloromethane;
DOI:10.1016/j.tetlet.2004.01.144

Reference yield:

: 635678-93-2
2-azido-N,N-diethyl-4,5-O-isopropylidene-7-O-trityl-D-glycero-D-allo-heptonamide

: 688321-44-0
(2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide

Guidance literature:: Multi-step reaction with 2 steps

1: 31 percent / NaH; TBAI / tetrahydrofuran / 144 h / 20 °C

2: 64 percent / TFA / CH₂Cl₂

With tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2004.01.144

Reference yield:

: 180591-23-5
(2S,3R)-3-[(4S,5R)-5-((R)-1-Hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxirane-2-carboxylic acid diethylamide

: 688321-44-0
(2R,3S)-2-Azido-3-benzyloxy-3-[(4S,5R)-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-N,N-diethyl-propionamide

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / NaN₃; AcOH / dimethylformamide

2: 31 percent / NaH; TBAI / tetrahydrofuran / 144 h / 20 °C

3: 64 percent / TFA / CH₂Cl₂

With sodium azide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.01.144