4H-1,3-Dioxolo4,5-cpyrrole-4-acetonitrile, 6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, (3aS,4S,6R,6aR)-

Base Information

• Chemical Name: 4H-1,3-Dioxolo4,5-cpyrrole-4-acetonitrile, 6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, (3aS,4S,6R,6aR)-
• CAS No.: 222631-08-5
• Molecular Formula: C16H30 N2 O3 Si
• Molecular Weight: 326.511
• Mol file: 222631-08-5.mol

Synonyms:4H-1,3-Dioxolo4,5-cpyrrole-4-acetonitrile, 6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, (3aS,4S,6R,6aR)-

Chemical Property of 4H-1,3-Dioxolo4,5-cpyrrole-4-acetonitrile, 6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, (3aS,4S,6R,6aR)-

Chemical Property:

• PSA: 63.51000
• LogP: 3.11118

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4H-1,3-Dioxolo4,5-cpyrrole-4-acetonitrile, 6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, (3aS,4S,6R,6aR)-

There total 14 articles about 4H-1,3-Dioxolo4,5-cpyrrole-4-acetonitrile, 6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, (3aS,4S,6R,6aR)- 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:

2-((3aS,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)acetonitrile (1610426-21-5) → 2-((3aS,4S,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo [4,5-c]pyrrol-4-yl)acetonitrile (222631-08-5)

Guidance literature:

With acetic acid; zinc; at 20 ℃; for 6h;

Reference yield:

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-31-7) → 2-((3aS,4S,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo [4,5-c]pyrrol-4-yl)acetonitrile (222631-08-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / SeO₂; aq. H₂O₂ / acetone / cooling

2: n-BuLi / tetrahydrofuran / 0.5 h / -70 °C

3: Zn; AcOH / 6 h

With n-butyllithium; selenium(IV) oxide; dihydrogen peroxide; acetic acid; zinc; In tetrahydrofuran; acetone;

DOI:10.1021/jo035744k

Reference yield:

(3aR,4S,6aS)-4-((tert-butyldimethylsilyl)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 5-oxide (607389-17-3) → 2-((3aS,4S,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo [4,5-c]pyrrol-4-yl)acetonitrile (222631-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: n-BuLi / tetrahydrofuran / 0.5 h / -70 °C

2: Zn; AcOH / 6 h

With n-butyllithium; acetic acid; zinc; In tetrahydrofuran;

DOI:10.1021/jo035744k

upstream raw materials:

lithioacetonitrile

(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

[(3aS,4S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-acetonitrile

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

Downstream raw materials:

(3aR,4R,6S,6aS)-tert-butyl 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-(cyanomethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

N-tert-butoxycarbonyl-2,3,6-trideoxy-3,6-imino-D-allo-heptononitrile

N-tert-butoxycarbonyl-3,6-imino-4,5-O-isopropylidene-2,3,6-trideoxy-D-allo-heptononitrile

forodesine