(S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

Base Information

• Chemical Name: (S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol
• CAS No.: 1453285-70-5
• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.375
• Mol file: 1453285-70-5.mol

Synonyms:(S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

Chemical Property of (S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

There total 4 articles about (S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol 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: 92.0%

5-O-benzyl-2,3,4-trideoxy-6,7-O-isopropylidene-D-erythro-hept-2-enoic acid ethyl ester (111689-71-5) → (S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol (1453285-70-5)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2013.07.072

Reference yield:

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (79364-35-5) → (S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol (1453285-70-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C / Inert atmosphere

2.1: ozone / dichloromethane / -78 °C

2.2: 2 h / 0 °C

3.1: benzene / 2 h / 20 °C

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C

With sodium hydride; diisobutylaluminium hydride; ozone; In tetrahydrofuran; dichloromethane; toluene; mineral oil; benzene; 3.1: |Wittig Olefination;

DOI:10.1016/j.tet.2013.07.072

Reference yield:

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane (87604-53-3) → (S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol (1453285-70-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ozone / dichloromethane / -78 °C

1.2: 2 h / 0 °C

2.1: benzene / 2 h / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C

With diisobutylaluminium hydride; ozone; In dichloromethane; toluene; benzene; 2.1: |Wittig Olefination;

DOI:10.1016/j.tet.2013.07.072

upstream raw materials:

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

5-O-benzyl-2,3,4-trideoxy-6,7-O-isopropylidene-D-erythro-hept-2-enoic acid ethyl ester

(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

Downstream raw materials:

((2R,3R)-3-((S)-2-(benzyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)oxiran-2-yl)methanol

(R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane

((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol

(((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methoxy)(tert-butyl)dimethylsilane