tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate

Base Information

• Chemical Name: tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate
• CAS No.: 505085-60-9
• Molecular Formula: C₁₈H₂₇NO₅S
• Molecular Weight: 369.482

Synonyms:tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate

Chemical Property of tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate

Chemical Property:

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Technology Process of tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate

There total 1 articles about tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate 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: 85.0%

(S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (399559-48-9) → tert-butyl (1'S,2'R,RS)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate (505085-60-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 3h;

DOI:10.1002/1099-0690(200301)2003:1<217::AID-EJOC217>3.0.CO;2-W

Reference yield: 90.0%

2,2-dimethoxy-propane (77-76-9) + tert-butyl (1'S,2'R,RS)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate (505085-60-9) → tert-butyl (4R,5S,RS)-2,2-dimethyl-4-{2-[(4-methylphenyl)sulfinyl]-2-propenyl}-1,3-dioxan-5-ylcarbamate (505085-61-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 0.5h;

DOI:10.1002/1099-0690(200301)2003:1<217::AID-EJOC217>3.0.CO;2-W

Reference yield:

tert-butyl (1'S,2'R,RS)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate (505085-60-9) → tert-butyl (4aS,7RS,8aR,RS)-2,2-dimethyl-7-[(4-methylphenyl)sulfinyl]hexahydro-5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pTsOH / acetone / 0.5 h / 20 °C

2: 93 percent / NaH / dimethylformamide / 0.5 h / 20 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetone;

DOI:10.1002/1099-0690(200301)2003:1<217::AID-EJOC217>3.0.CO;2-W

upstream raw materials:

(S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

tert-butyl (4R,5S,R_S)-2,2-dimethyl-4-{2-[(4-methylphenyl)sulfinyl]-2-propenyl}-1,3-dioxan-5-ylcarbamate

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