(2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol

Base Information

• Chemical Name: (2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol
• CAS No.: 208168-09-6
• Molecular Formula: C₂₉H₃₂O₄
• Molecular Weight: 444.571
• Mol file: 208168-09-6.mol

Synonyms:(2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol

Chemical Property of (2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol

There total 2 articles about (2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-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: 85.0%

allyltributylstanane (24850-33-7) + 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (119927-20-7) → (2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol (208168-09-6)

Guidance literature:

With 4 A molecular sieve; magnesium bromide; In dichloromethane; at -78 - -40 ℃; for 4h;

DOI:10.1016/S0957-4166(01)00262-2

Reference yield:

3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (119927-20-7) + allyl bromide (106-95-6) → (2R)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol + (2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol (208168-09-6)

Guidance literature:

With tetrahydrofuran; indium; water; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/S0957-4166(98)00103-7

Reference yield:

(2S)-1-O-trityl-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-pentene-1,2-diol (208168-09-6) → (2S)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(trityloxy)methyl]-5,6-dihydro-2H-pyran-2-one

Guidance literature:

Multi-step reaction with 3 steps

1: KH; tetrabutylammonium iodide / tetrahydrofuran / Heating

2: 87 percent / [Cl₂Ru(PCy₃)2=CHPh] / CH₂Cl₂ / Heating

3: 65 percent / CrO₃; 3,5-dimethylpyrazole / CH₂Cl₂ / 1 h / -20 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; Grubbs catalyst first generation; tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(03)00584-2

upstream raw materials:

3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose

allyl bromide

allyltributylstanane

Downstream raw materials:

(2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(trityloxy)methyl]-3,6-dihydro-2H-pyran