(3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene

Base Information

• Chemical Name: (3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene
• CAS No.: 256650-53-0
• Molecular Formula: C₂₁H₂₇NO₄S
• Molecular Weight: 389.516

Synonyms:(3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene

Chemical Property of (3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene

Chemical Property:

Purity/Quality:

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Technology Process of (3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene

There total 4 articles about (3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene 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: 55.0%

benzyl bromide (100-39-0) + (2S,3S/R)-2-(2,4,6-Trimethylphenylsulfonylamino)pent-4-ene-1,3-diol (256650-52-9) → (3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene (256650-53-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1039/a904671b

Reference yield:

2-mesitylenesulphonyl chloride (773-64-8) → (3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene (256650-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: DIPEA / CHCl₃ / 15 h / 0 °C

2: 55 percent / NaH / tetrahydrofuran / 2 h / 0 °C

With sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; 1: Substitution / 2: Etherification;

DOI:10.1039/a904671b

Reference yield:

(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-<1-hydroxy-2-propenyl>oxazolidine (256650-51-8) → (3S/R,4S)-5-Benzyloxy-3-hydroxy-4-(2,4,6-trimethylphenylsulfonylamino)pent-1-ene (256650-53-0)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA; H₂O / 1 h / 0 °C

2: DIPEA / CHCl₃ / 15 h / 0 °C

3: 55 percent / NaH / tetrahydrofuran / 2 h / 0 °C

With water; sodium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; chloroform; 1: Ring cleavage / 2: Substitution / 3: Etherification;

DOI:10.1039/a904671b

upstream raw materials:

benzyl bromide

(2S,3S/R)-2-(2,4,6-Trimethylphenylsulfonylamino)pent-4-ene-1,3-diol

2-mesitylenesulphonyl chloride

(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-<1-hydroxy-2-propenyl>oxazolidine

Downstream raw materials:

Methyl (2E,4S,5S)-6-benzyloxy-4-trifluoroacetoxy-5-(2,4,6-trimethylphenylsulfonylamino)hex-2-enoate

6-Benzyloxy-(2E,4S,5S)-N-methyl-4-(methylsulfonyloxy)-5-(2,4,6-trimethylphenylsulfonylamino)hex-2-enamide

(2E,4R,5R)-6-Benzyloxy-N-methyl-4,5-[(2,4,6-trimethylphenylsulfonyl)epimino]hex-2-enamide

Methyl (2E,4R,5R)-6-benzyloxy-4,5-[(2,4,6-trimethylphenylsulfonyl)epimino]hex-2-enoate

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