(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone

Base Information

• Chemical Name: (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone
• CAS No.: 159700-63-7
• Molecular Formula: C₁₈H₂₈N₂O₄Si
• Molecular Weight: 364.517
• Mol file: 159700-63-7.mol

Synonyms:(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone

Chemical Property of (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone

There total 4 articles about (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone 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: 78.0%

(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone (159622-45-4) → (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone (159700-63-7)

Guidance literature:

With pyridine; ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)89309-1

Reference yield:

(S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone (159622-41-0) → (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone (159700-63-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / lithium di-iso-propylamide, iso-amyl nitrite / tetrahydrofuran; hexane / 1 h / -78 °C

2: hydrogen / PtO₂ / ethyl acetate; H₂O / 12 h

3: 39 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 45 h / 0 °C

4: 78 percent / cerium ammonium nitrate, pyridine / acetonitrile; H₂O / 0.5 h / 0 °C

With pyridine; ammonium cerium(IV) nitrate; hydrogen; sodium carbonate; lithium diisopropyl amide; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; hexane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)89309-1

Reference yield:

(E)/(Z) (S) 1-(tert-butyldimethylsilyl)-3-(hydroxyimino)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone → (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone (159700-63-7)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen / PtO₂ / ethyl acetate; H₂O / 12 h

2: 39 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 45 h / 0 °C

3: 78 percent / cerium ammonium nitrate, pyridine / acetonitrile; H₂O / 0.5 h / 0 °C

With pyridine; ammonium cerium(IV) nitrate; hydrogen; sodium carbonate; platinum(IV) oxide; In tetrahydrofuran; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)89309-1

upstream raw materials:

(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

(S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

Downstream raw materials:

(3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone