(E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol

Base Information

• Chemical Name: (E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol
• CAS No.: 106976-85-6
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 106976-85-6.mol

Synonyms:(E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol

Chemical Property of (E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol

There total 9 articles about (E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol 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:

1,2-(isopropylidenedioxy)-5-acetoxy-7-phenylhept-6-en-4-one (106976-80-1,106976-81-2) → Acetic acid (E)-(R)-1-[(S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-hydroxy-ethyl]-3-phenyl-allyl ester (106976-84-5) + (E)-(2S,3R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol (106976-85-6)

Guidance literature:

With D-glucose; In ethanol; water; at 25 - 28 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; bakers' yeast;

DOI:10.1021/jo00386a034

Reference yield:

2-<2,3-(isopropylidenedioxy)propyl>-2-(1-hydroxy-3-phenyl-2-propenyl)-1,3-dithiane (106976-79-8,106976-94-7) → (E)-(2S,3R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol (106976-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) HgO, BF₃*Et₂O / 1.) pyridine, RT, 12 h, 2.) THF, H₂O, 23 deg C, 4 h

2: D-glucose / ethanol; H₂O / 12 h / 25 - 28 °C / bakers' yeast

With D-glucose; boron trifluoride diethyl etherate; mercury(II) oxide; In ethanol; water;

DOI:10.1021/jo00386a034

Reference yield:

2-<2,3-(isopropylidenedioxy)propyl>-1,3-dithiane (106976-78-7) → (E)-(2S,3R)-1-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol (106976-85-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / n-BuLi / tetrahydrofuran / 5 h

2: 2.) HgO, BF₃*Et₂O / 1.) pyridine, RT, 12 h, 2.) THF, H₂O, 23 deg C, 4 h

3: 1.) D-glucose, 2.) 2N NaOH / 1.) bakers' yeast, ethanol, water, 25-28 deg C, 12 h, 2.) methanol, 12 h

With sodium hydroxide; n-butyllithium; D-glucose; boron trifluoride diethyl etherate; mercury(II) oxide; In tetrahydrofuran;

DOI:10.1021/jo00386a034

upstream raw materials:

1,2-(isopropylidenedioxy)-5-acetoxy-7-phenylhept-6-en-4-one

2-<2,3-(isopropylidenedioxy)propyl>-2-(1-hydroxy-3-phenyl-2-propenyl)-1,3-dithiane

2-<2,3-(isopropylidenedioxy)propyl>-1,3-dithiane

Downstream raw materials:

Acetic acid (E)-(1S,2R)-2-acetoxy-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-phenyl-but-3-enyl ester

4-deoxy-D-lyxo-hexopyranose

Acetic acid (E)-(1S,2R)-2-acetoxy-1-(2,3-dihydroxy-propyl)-4-phenyl-but-3-enyl ester

Acetic acid (E)-(1S,2R)-2-acetoxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-phenyl-but-3-enyl ester