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

Base Information

Chemical Name:Benzoic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester
CAS No.:121964-16-7
Molecular Formula:C₂₀H₂₃N₃O₄
Molecular Weight:369.42
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Benzoic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester

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Technology Process of Benzoic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester

There total 5 articles about Benzoic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester 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: 87.0%

: 98-88-4
benzoyl chloride

: 121964-08-7
(2R,3S,4S)-5-Azido-3-O-benzyl-4-methylpentane-1,2,3-triol

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

Guidance literature:: With pyridine; dmap; In diethyl ether; at 0 ℃; for 1h;
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

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

Guidance literature:: Multi-step reaction with 5 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

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

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

Guidance literature:: Multi-step reaction with 4 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

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