(3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone

Base Information

• Chemical Name: (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone
• CAS No.: 113599-60-3
• Molecular Formula: C₁₈H₂₈N₂O₄Si
• Molecular Weight: 364.517
• Mol file: 113599-60-3.mol

Synonyms:(3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone

Chemical Property of (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone

There total 5 articles about (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-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:

(3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-2-azetidinone (86334-63-6) → (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone (113599-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / K₂S₂O₈, K₂HPO₄ / acetonitrile; H₂O / 4 h / 95 °C

2: 1.) Et₃N, 4-(dimethylamino)pyridine, 2.) KF / 1.) DMF, 1 h, 2.) HOAc, 1 h

With dmap; potassium fluoride; dipotassium hydrogenphosphate; dipotassium peroxodisulfate; triethylamine; In water; acetonitrile;

DOI:10.1021/jm00401a020

Reference yield:

(3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-formyl-2-azetidinone (86299-41-4) → (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone (113599-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄, Al₂O₃ / CH₂Cl₂ / 0.67 h

2: 69 percent / K₂S₂O₈, K₂HPO₄ / acetonitrile; H₂O / 4 h / 95 °C

3: 1.) Et₃N, 4-(dimethylamino)pyridine, 2.) KF / 1.) DMF, 1 h, 2.) HOAc, 1 h

With dmap; aluminum oxide; potassium fluoride; sodium tetrahydroborate; dipotassium hydrogenphosphate; dipotassium peroxodisulfate; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1021/jm00401a020

Reference yield:

C16H36N(1+)*C18H27N2O7SSi(1-) (1393717-48-0) → (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone (113599-60-3)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1016/j.bmcl.2012.06.040

upstream raw materials:

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

tert-butyldimethylsilyl chloride

(3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-formyl-2-azetidinone

(3S,4S)-3-(benzyloxycarboxamido)-1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-2-azetidinone

Downstream raw materials:

(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-(tritylamino)-2-azetidinone

allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-(tritylamino)-1-azetidinyl>acetate

allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-4-chlorobutanoate

allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate