(E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester
• CAS No.: 133604-42-9
• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.439

Synonyms:(E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester

Chemical Property of (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester

There total 2 articles about (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester 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:

(2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol (100572-69-8) → (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester (133604-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂

2: 1.) NaH / 1.) THF, RT, 2 h, 2.) RT, 24 h

With sodium hydride; ozone; triphenylphosphine;

DOI:10.1021/ja00011a025

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (2R,3S)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde (120040-77-9,133604-44-1) → (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester (133604-42-9)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, RT, 2 h, 2.) RT, 24 h;

DOI:10.1021/ja00011a025

Reference yield:

(E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester (133604-42-9) → (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-en-1-ol (133604-43-0,133695-41-7)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; toluene; at -5 ℃; for 4h; Yield given;

DOI:10.1021/ja00011a025

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(2R,3S)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde

(2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol

Downstream raw materials:

(E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-en-1-ol

(R)-4-((E)-(1S,2S)-1-Benzyloxy-5-bromo-2-methyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane

(2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-5-(hydroxymethyl)-4-methyloctane-1,2,3,6,7-pentol

(2'R,2S,3S,4S,5R)-4-(benzyloxy)-2-((2',2-isopropylidenedioxy)propyl)-3-methyl-5,6-(isopropylidenedioxy)hexanal

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