(R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-ol

Base Information

• Chemical Name: (R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-ol
• CAS No.: 1235459-86-5
• Molecular Formula: C₁₉H₂₈O₂S₂
• Molecular Weight: 352.562
• Mol file: 1235459-86-5.mol

Synonyms:(R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-ol

Chemical Property of (R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-ol

There total 1 articles about (R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-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: 97.0%

2-(pent-2-en-2-yl)-1,3-dithiane + (R)-benzyl glycidol (14618-80-5) → (R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-ol (1235459-86-5)

Guidance literature:

2-(pent-2-en-2-yl)-1,3-dithiane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.583333h; Inert atmosphere;

(R)-benzyl glycidol; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; hexane; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.069

Reference yield: 93.0%

(R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-ol (1235459-86-5) + t-butyldimethylsiyl triflate (69739-34-0) → (R,E)-((1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)propan-2-yl)oxy)(tert-butyl)dimethylsilane (1235460-05-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol101103q

Reference yield:

(R,E)-1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)-propan-2-ol (1235459-86-5) → (2R,4R,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol (1235460-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C

2.1: benzeneseleninic anhydride; methyloxirane / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere

With 2,6-dimethylpyridine; dimethylsulfide borane complex; benzeneseleninic anhydride; methyloxirane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2011.09.069

upstream raw materials:

(R)-benzyl glycidol

Downstream raw materials:

(R,E)-((1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)propan-2-yl)oxy)(tert-butyl)dimethylsilane

(R,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-one

(2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

(2R,4R,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol