(3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone

Base Information

• Chemical Name: (3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone
• CAS No.: 108404-45-1
• Molecular Formula: C₁₅H₁₉ClO₃
• Molecular Weight: 282.767
• Mol file: 108404-45-1.mol

Synonyms:

Chemical Property of (3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone

There total 8 articles about (3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone 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:

benzyl bromide (100-39-0) → (3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone (108404-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium hydride / 1.) DMF, 1 h, r.t.; 2.) DMF

2: sat. hydrogen chloride / acetic acid / 48 h / Ambient temperature

With hydrogenchloride; sodium hydride; In acetic acid;

Reference yield:

(E)(S)-4-(3-hydroxy-2-methylpropenyl)-2,2-dimethyl[1,3]dioxolane (108404-41-7) → (3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone (108404-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pivalic acid / 3 h / 140 °C

2: conc. hydrochloric acid / ethanol / 24 h / Ambient temperature

3: 1.) sodium hydride / 1.) DMF, 1 h, r.t.; 2.) DMF

4: sat. hydrogen chloride / acetic acid / 48 h / Ambient temperature

With hydrogenchloride; sodium hydride; Trimethylacetic acid; In ethanol; acetic acid;

Reference yield:

(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester (81997-76-4) → (3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone (108404-45-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.23 M di-isobutylaluminium hydride / tetrahydrofuran; toluene / 0.17 h

2: pivalic acid / 3 h / 140 °C

3: conc. hydrochloric acid / ethanol / 24 h / Ambient temperature

4: 1.) sodium hydride / 1.) DMF, 1 h, r.t.; 2.) DMF

5: sat. hydrogen chloride / acetic acid / 48 h / Ambient temperature

With hydrogenchloride; diisobutylaluminum hydride; sodium hydride; Trimethylacetic acid; In tetrahydrofuran; ethanol; acetic acid; toluene;

upstream raw materials:

(3R,4S)-5-benzyloxy-4-hydroxy-3-isopropenylpentanoic acid lactone

benzyl bromide

(E)(S)-4-(3-hydroxy-2-methylpropenyl)-2,2-dimethyl[1,3]dioxolane

(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester

Downstream raw materials:

(1S,3R)-3-(2-benzyloxy-1-hydroxyethyl)-2,2-dimethylcyclopropanecarboxylic acid lactone