[3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one

Base Information

• Chemical Name: [3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one
• CAS No.: 318488-47-0
• Molecular Formula: C₁₉H₂₃NO₅
• Molecular Weight: 345.395

Synonyms:[3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one

Chemical Property of [3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of [3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one

There total 4 articles about [3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one 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%

(4S)-3-(2-allyloxyethanoyl)-4-benzyloxazolidin-2-one (197721-28-1) + crotonaldehyde (123-73-9,4170-30-3) → [3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one (318488-47-0)

Guidance literature:

With titanium tetrachloride; (-)-sparteine; In dichloromethane; at -78 - 0 ℃; for 0.5h;

DOI:10.1021/jo005535p

Reference yield:

2-(allyloxy)acetic acid (22577-14-6) → [3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one (318488-47-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / diethyl ether / 1 h / -78 - 0 °C

2: 10.0 g / n-BuLi / tetrahydrofuran; diethyl ether / 0.75 h / -78 - 0 °C

3: 87 percent / TiCl₄; (-)-sparteine / CH₂Cl₂ / 0.5 h / -78 - 0 °C

With n-butyllithium; titanium tetrachloride; triethylamine; (-)-sparteine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo005535p

Reference yield:

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) → [3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one (318488-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 10.0 g / n-BuLi / tetrahydrofuran; diethyl ether / 0.75 h / -78 - 0 °C

2: 87 percent / TiCl₄; (-)-sparteine / CH₂Cl₂ / 0.5 h / -78 - 0 °C

With n-butyllithium; titanium tetrachloride; (-)-sparteine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo005535p

upstream raw materials:

(4S)-3-(2-allyloxyethanoyl)-4-benzyloxazolidin-2-one

crotonaldehyde

2-(allyloxy)acetic acid

(S)-4-Benzyl-2-oxazolidinone

Downstream raw materials:

Benzoic acid (2S,5S)-5-(2-amino-6-chloro-purin-9-yl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

(2R,3R)-2-allyloxyhept-4-en-1,3-diol dibenzoate

2-hydroxymethyl-3,5-dihydro-2H-pyran-3-ol dibenzoate

(S)-4-Benzyl-3-((2S,3R)-3-hydroxy-3,6-dihydro-2H-pyran-2-carbonyl)-oxazolidin-2-one

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