(4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane
• CAS No.: 156145-69-6
• Molecular Formula: C₂₃H₂₉NO₃Si
• Molecular Weight: 395.574
• Mol file: 156145-69-6.mol

Synonyms:(4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane

There total 8 articles about (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-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: 87.0%

(4S,5S)-5-tert-butyl(diphenyl)silyloxymethyl-4-carbamoyl-2,2-dimethyl-1,3-dioxolane (293314-31-5) → (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane (156145-69-6)

Guidance literature:

With pyridine; (CF₃CO₂)2O; at 20 ℃; for 4h;

DOI:10.1016/S0957-4166(00)00216-0

Reference yield:

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose oxime (156145-68-5) → (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane (156145-69-6)

Guidance literature:

With 1,1'-carbonyldiimidazole; Yield given;

DOI:10.1016/S0957-4166(00)86190-X

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane (156145-69-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 15 h

2: NH₃ / ethanol / 72 h / 20 °C

3: 87 percent / (CF₃CO₂)2O; pyridine / 4 h / 20 °C

With pyridine; dmap; (CF₃CO₂)2O; ammonia; triethylamine; In ethanol; dichloromethane; 1: Condensation / 2: amidation / 3: Dehydration;

DOI:10.1016/S0957-4166(00)00216-0

upstream raw materials:

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose oxime

(4S,5S)-5-tert-butyl(diphenyl)silyloxymethyl-4-carbamoyl-2,2-dimethyl-1,3-dioxolane

methyl (4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2S,3S,4R)-4-(benzylamino)-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

6-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-[2,2']bipyridinyl

6-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyridine-2-carbonitrile

Toluene-4-sulfonic acid (4S,5S)-5-[2,2']bipyridinyl-6-yl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester