(R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane
• CAS No.: 796128-14-8
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333
• Mol file: 796128-14-8.mol

Synonyms:(R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane

Chemical Property of (R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane

There total 2 articles about (R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane 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: 83.0%

benzyl bromide (100-39-0) + 1-[2',2'-dimethyl-(4'R)-1',3'-dioxolan-4'-yl]-(1S)-3-butyn-1-ol (149859-05-2) → (R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane (796128-14-8)

Guidance literature:

1-[2',2'-dimethyl-(4'R)-1',3'-dioxolan-4'-yl]-(1S)-3-butyn-1-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/ol048165q

Reference yield: 68.0%

benzyl bromide (100-39-0) + 2,2'-dimethyl-1-(4'(R)-1',3'-dioxacyclopentyl)-but-3-yn-1(S/R)-ol (383135-46-4) → (R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane (796128-14-8)

Guidance literature:

2,2'-dimethyl-1-(4'(R)-1',3'-dioxacyclopentyl)-but-3-yn-1(S/R)-ol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h; Cooling with ice; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 0 - 55 ℃;

DOI:10.1055/s-0037-1611904

Reference yield: 65.0%

ortho-nitrofluorobenzene (1493-27-2,127723-77-7) + (R)-4-((S)-1-(benzyloxy)but-3-yn-1-yl)-2,2-dimethyl-1,3-dioxolane (796128-14-8) → 3,4-O-isopropylidene-2-O-benzyl-1-deoxy-1-C-[(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)]-D-erythritol (1160926-68-0)

Guidance literature:

With sodium azide; copper(ll) sulfate pentahydrate; sodium carbonate; sodium L-ascorbate; L-proline; In water; dimethyl sulfoxide; at 70 ℃; for 24h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2009.03.035

upstream raw materials:

benzyl bromide

1-[2',2'-dimethyl-(4'R)-1',3'-dioxolan-4'-yl]-(1S)-3-butyn-1-ol

2,2'-dimethyl-1-(4'(R)-1',3'-dioxacyclopentyl)-but-3-yn-1(S/R)-ol

Downstream raw materials:

1,5-anhydro-4,6-di-O-benzyl-D-erythro-hex-1-enitol

(3-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-methanol

3,4-O-isopropylidene-2-O-benzyl-1-deoxy-1-C-[(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)]-D-erythritol