(2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane

Base Information

• Chemical Name: (2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane
• CAS No.: 221086-13-1
• Molecular Formula: C₂₉H₃₀O₄
• Molecular Weight: 442.555
• Mol file: 221086-13-1.mol

Synonyms:(2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane

Chemical Property of (2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane

There total 1 articles about (2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[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:

phenylpropargyl aldehyde diethyl acetal (6142-95-6) + (3S,4R)-1,6-Bis-benzyloxy-hexane-3,4-diol → (2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane (221086-13-1) + (2R,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(98)02387-9

Reference yield: 80.0%

(1-tert-butylsulfanyl-vinyloxy)trimethylsilane (63584-47-4) + (2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane (221086-13-1) → 3-[4-benzyloxy-1-(2-benzyloxy-ethyl)-2-hydroxy-butoxy]-5-phenyl-pent-4-ynethioic acid S-tert-butyl ester

Guidance literature:

With chiral cyclic oxazaborolidine -C(Bn)-C(O)-O-B(Ph)-N(Ts)-; In dichloromethane; at -78 ℃; for 15h;

DOI:10.1016/S0040-4039(98)02387-9

Reference yield:

(2S,4R,5S)-4,5-Bis-(2-benzyloxy-ethyl)-2-phenylethynyl-[1,3]dioxolane (221086-13-1) → (2R,3R)-2,3-Bis-(2-benzyloxy-ethyl)-oxirane

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / chiral cyclic oxazaborolidine -C(Bn)-C(O)-O-B(Ph)-N(Ts)- / CH₂Cl₂ / 15 h / -78 °C

2: Et₃N / CH₂Cl₂ / Ambient temperature

3: K₂CO₃ / methanol

With potassium carbonate; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(98)02387-9

upstream raw materials:

phenylpropargyl aldehyde diethyl acetal