(2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol

Base Information

Chemical Name:(2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol
CAS No.:121964-13-4
Molecular Formula:C₂₁H₂₅N₃O₆S
Molecular Weight:447.512
Hs Code.:

Synonyms:(2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol

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Chemical Property of (2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol

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Technology Process of (2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol

There total 6 articles about (2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol 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: 86.0%

: 124-63-0
methanesulfonyl chloride

: 121964-16-7
Benzoic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester

: 121964-13-4
(2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol

Guidance literature:: With pyridine; dmap; In tetrahydrofuran; 1.) 14 h, 20 degC, 2.) 2 h, 45 degC;
DOI:10.1021/ja00201a033

Reference yield:

: 100572-69-8
(2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol

: 121964-13-4
(2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, -78 degC, 2.) 20 degC

2: 92 percent / DMAP, pyridine / tetrahydrofuran / 1.) 14 h, 20 degC, 2.) 2 h, 45 degC

3: 91 percent / NaN₃ / dimethylformamide / 24 h / 45 °C

4: 94 percent / p-TsOH / methanol / 12 h / 45 °C

5: 87 percent / DMAP, pyridine / diethyl ether / 1 h / 0 °C

6: 86 percent / DMAP, pyridine / tetrahydrofuran / 1.) 14 h, 20 degC, 2.) 2 h, 45 degC

With pyridine; dmap; sodium tetrahydroborate; sodium azide; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja00201a033

Reference yield:

: 121964-06-5
(2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol

: 121964-13-4
(2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / DMAP, pyridine / tetrahydrofuran / 1.) 14 h, 20 degC, 2.) 2 h, 45 degC

2: 91 percent / NaN₃ / dimethylformamide / 24 h / 45 °C

3: 94 percent / p-TsOH / methanol / 12 h / 45 °C

4: 87 percent / DMAP, pyridine / diethyl ether / 1 h / 0 °C

5: 86 percent / DMAP, pyridine / tetrahydrofuran / 1.) 14 h, 20 degC, 2.) 2 h, 45 degC

With pyridine; dmap; sodium azide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja00201a033