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

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester
CAS No.:121964-24-7
Molecular Formula:C₂₀H₂₅N₃O₅S
Molecular Weight:419.502
Hs Code.:

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

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

There total 5 articles about Toluene-4-sulfonic 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:

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

: 121964-24-7
Toluene-4-sulfonic 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: DMAP, pyridine / 14 h / 0 - 22 °C

With pyridine; dmap; sodium tetrahydroborate; sodium azide; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol; 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

: 121964-24-7
Toluene-4-sulfonic 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: DMAP, pyridine / 14 h / 0 - 22 °C

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

Reference yield:

: (R)-4-((1S,2S)-3-Azido-1-benzyloxy-2-methyl-propyl)-2,2-dimethyl-[1,3]dioxolane

: 121964-24-7
Toluene-4-sulfonic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / p-TsOH / methanol / 12 h / 45 °C

2: DMAP, pyridine / 14 h / 0 - 22 °C

With pyridine; dmap; toluene-4-sulfonic acid; In methanol;
DOI:10.1021/ja00201a033