tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate

Base Information

• Chemical Name: tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate
• CAS No.: 308795-89-3
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374

Synonyms:tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate

Chemical Property of tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate

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Technology Process of tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate

There total 3 articles about tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate 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: 64.0%

tert-butyl (4S)-4-[(1R)-1-hydroxy-3-(4-methylphenyl)-2-propynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (308795-88-2) → tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate (308795-89-3)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 20 ℃;

DOI:10.1021/jm000939v

Reference yield:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate (308795-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

1.2: 70 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 64 percent / p-TsOH; MeOH / 20 °C

With methanol; n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane;

DOI:10.1021/jm000939v

Reference yield:

4-n-methylphenylacetylene (766-97-2) → tert-butyl (1S,2R)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butynylcarbamate (308795-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

1.2: 70 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 64 percent / p-TsOH; MeOH / 20 °C

With methanol; n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane;

DOI:10.1021/jm000939v

upstream raw materials:

tert-butyl (4S)-4-[(1R)-1-hydroxy-3-(4-methylphenyl)-2-propynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

4-n-methylphenylacetylene

Downstream raw materials:

(2S,3R,4E)-2-amino-5-(4-methylphenyl)-4-pentene-1,3-diol

tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-4-(4-methylphenyl)-3-butenylcarbamate

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