[(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

Base Information

• Chemical Name: [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol
• CAS No.: 366011-44-1
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.392
• Mol file: 366011-44-1.mol

Synonyms:[(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

Chemical Property of [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

There total 5 articles about [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol 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: 93.0%

(4S,5S)-4-((Z)-(R)-1-Benzyloxy-7-triisopropylsilanyl-hept-4-ene-2,6-diynyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolane (366011-51-0) → [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (366011-44-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 - 0 ℃; for 4h;

DOI:10.1560/7J4F-D8BG-3FQR-E3TD

Reference yield:

benzyl bromide (100-39-0) → [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (366011-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NaH / tetrahydrofuran / 17 h / 21 °C

2: 93 percent / TBAF / tetrahydrofuran / 4 h / -78 - 0 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1560/7J4F-D8BG-3FQR-E3TD

Reference yield:

(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (108817-97-6) → [(4S,5S)-5-((Z)-(R)-1-Benzyloxy-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (366011-44-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / 0.33 h

1.2: 86 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 88 percent / NaH / tetrahydrofuran / 17 h / 21 °C

3.1: 93 percent / TBAF / tetrahydrofuran / 4 h / -78 - 0 °C

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1560/7J4F-D8BG-3FQR-E3TD

upstream raw materials:

(4S,5S)-4-((Z)-(R)-1-Benzyloxy-7-triisopropylsilanyl-hept-4-ene-2,6-diynyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolane

benzyl bromide

(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

(Z)-hex-3-en-1,5-diynyl-triisopropylsilane

Downstream raw materials:

(4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde