(S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane

Base Information

• Chemical Name: (S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane
• CAS No.: 1053718-67-4
• Molecular Formula: C₃₆H₄₄O₆
• Molecular Weight: 572.742
• Mol file: 1053718-67-4.mol

Synonyms:(S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane

Chemical Property of (S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane

There total 1 articles about (S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-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:

1,1-dibromomethane (74-95-3) + 3-(2,2-dimethyl-[1,3]dioxolan-4-yl)propionic acid 2,3-bis(benzyloxy)-1-(benzyloxymethyl)pent-4-enyl ester → (S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane (1053718-67-4)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; lead(II) chloride; In tetrahydrofuran; dichloromethane; at 60 ℃;

DOI:10.1021/jo040254t

Reference yield:

(S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane (1053718-67-4) → (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4-dihydro-2H-pyran

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 60 ℃; for 2h;

DOI:10.1021/jo040254t

Reference yield:

(S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane (1053718-67-4) → (2R,3S,4R)-6-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran

Guidance literature:

Multi-step reaction with 3 steps

1: second-generation Grubbs catalyst / toluene / 2 h / 60 °C

2: H₂ / Pd/C / ethanol; ethyl acetate / 6 h / 2844.31 Torr

3: NaH; Bu₄NI / dimethylformamide / 6 h / 0 - 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium on activated charcoal; In ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo040254t

upstream raw materials:

1,1-dibromomethane

Downstream raw materials:

(Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester