(2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol

Base Information

Chemical Name:(2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol
CAS No.:929006-75-7
Molecular Formula:C₂₄H₃₂N₄O₄
Molecular Weight:440.542
Hs Code.:

Synonyms:(2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol

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Chemical Property of (2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol

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Technology Process of (2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol

There total 8 articles about (2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol 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:

: 929006-73-5
((2S,3S)-3-(((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)methyl)oxiran-2-yl)methanol

: 3-azido-4-(5-dibenzylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-butane-1,2-diol

: 929006-75-7
(2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol

Guidance literature:: ((2S,3S)-3-(((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)methyl)oxiran-2-yl)methanol; With Trimethyl borate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 4h;
DOI:10.1021/ol062804a

Reference yield:

: 929006-83-7
(2S,3R)-2-(dibenzylamino)hept-5-yne-1,3,7-triol

: 929006-75-7
(2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: CSA / acetone / 2 h / 50 °C

1.2: 79 percent / acetic acid / tetrahydrofuran; H₂O / 1 h / 20 °C

2.1: 78 percent / Red-Al / diethyl ether; toluene / 20 h / -10 - 20 °C

3.1: mCPBA / CH₂Cl₂ / 0.07 h / 20 °C

4.1: 41.2 mg / imidazole / dimethylformamide / 4 h / 20 °C

5.1: 88 percent / TBAF / tetrahydrofuran / 18 h / -20 °C

6.1: B(OMe)3 / dimethylformamide / 0.5 h / 20 °C

6.2: 10.2 mg / NaN₃ / dimethylformamide / 4 h / 50 °C

With 1H-imidazole; Trimethyl borate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ol062804a

Reference yield:

: 929006-71-3
(E)-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)but-2-en-1-ol

: 929006-75-7
(2R,3S)-2-azido-4-((4R,5S)-5-(dibenzylamino)-2,2-dimethyl-1,3-dioxan-4-yl)butane-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: mCPBA / CH₂Cl₂ / 0.07 h / 20 °C

2.1: 41.2 mg / imidazole / dimethylformamide / 4 h / 20 °C

3.1: 88 percent / TBAF / tetrahydrofuran / 18 h / -20 °C

4.1: B(OMe)3 / dimethylformamide / 0.5 h / 20 °C

4.2: 10.2 mg / NaN₃ / dimethylformamide / 4 h / 50 °C

With 1H-imidazole; Trimethyl borate; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol062804a