(2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate

Base Information

Chemical Name:(2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate
CAS No.:889664-12-4
Molecular Formula:C₂₁H₂₃F₂N₃O₇S
Molecular Weight:499.492
Hs Code.:

Synonyms:(2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate

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Chemical Property of (2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate

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Technology Process of (2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate

There total 11 articles about (2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate 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:

: 889664-11-3
(2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5,6-dihydroxyhex-1-yl benzoate

: 124-63-0
methanesulfonyl chloride

: 889664-12-4
(2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate

Guidance literature:: With 2,3,5-trimethyl-pyridine; In dichloromethane; at 0 ℃; for 20h;
DOI:10.1021/jm060066q

Reference yield:

: 885621-52-3
(2S,4R,5R)-4-O-benzyl-1-O-benzoyl-3,3-difluoro-5,6-O-isopropylidenehexane-1,2,4,5,6-pentol

: 889664-12-4
(2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / CH₂Cl₂ / 2 h / -25 °C

2: 2.66 g / sodium azide / dimethylformamide / 20 °C

3: 95 percent / aq. AcOH / 3 h / 50 °C

4: 86 percent / imidazole / dimethylformamide / 1 h / 0 °C

5: 93 percent / triethylamine; DMAP / CH₂Cl₂ / 12 h / 20 °C

6: 89 percent / acetic acid / tetrahydrofuran; H₂O / 48 h / 20 °C

7: 75 percent / 24 h / 140 °C

8: 97 percent / HCl / methanol; CH₂Cl₂ / 10 h / 20 °C

9: collidine / CH₂Cl₂ / 20 h / 0 °C

With pyridine; 1H-imidazole; 2,3,5-trimethyl-pyridine; hydrogenchloride; dmap; sodium azide; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm060066q

Reference yield:

: 889663-97-2
(2R,4R)-2-azido-4-O-benzyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobut-1-yl benzoate

: 889664-12-4
(2R,4R,5S)-2-azido-4-O-benzyl-3,3-difluoro-5-hydroxy-6-(methylsulfonyloxy)hex-1-yl benzoate

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / aq. AcOH / 3 h / 50 °C

2: 86 percent / imidazole / dimethylformamide / 1 h / 0 °C

3: 93 percent / triethylamine; DMAP / CH₂Cl₂ / 12 h / 20 °C

4: 89 percent / acetic acid / tetrahydrofuran; H₂O / 48 h / 20 °C

5: 75 percent / 24 h / 140 °C

6: 97 percent / HCl / methanol; CH₂Cl₂ / 10 h / 20 °C

7: collidine / CH₂Cl₂ / 20 h / 0 °C

With 1H-imidazole; 2,3,5-trimethyl-pyridine; hydrogenchloride; dmap; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm060066q