p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate

Base Information

• Chemical Name: p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate
• CAS No.: 85253-98-1
• Molecular Formula: C₂₁H₃₁IN₂O₇Si
• Molecular Weight: 578.476
• Mol file: 85253-98-1.mol

Synonyms:

Chemical Property of p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate

There total 18 articles about p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate 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: 67.0%

p-nitrobenzyl glyoxylate monohydrate (83654-96-0) + <3S-<3α(S*),4β>>-3-(1-t-butyldimethylsilyloxyethyl)-4-iodomethyl-2-azetidinone (84362-42-5) → p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate (85253-98-1,107983-03-9,107983-04-0)

Guidance literature:

In benzene; for 10h; Heating;

DOI:10.1246/bcsj.59.1887

Reference yield:

(3S,4R)-3-<(R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-(methylsulfonyl)-2-azetidinone (80813-18-9) → p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate (85253-98-1,107983-03-9,107983-04-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / tetrabutylammonium bromide / benzene; H₂O / 24 h

2: 85 percent / 30percent aq. H₂O₂, 0.5M Na₂CO₃ / H₂O; acetone / 0.5 h / Ambient temperature

3: NaOH / ethanol; H₂O / 1 h / 50 °C

4: ethyl acetate; diethyl ether

5: 78 percent / NaBH₄ / H₂O; tetrahydrofuran / 0.25 h / 0 °C

6: 68 percent / pyridine / tetrahydrofuran; CH₂Cl₂

7: 95 percent / NaI / acetone / 7 h / 60 °C

8: 67 percent / benzene / 10 h / Heating

With pyridine; sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; sodium carbonate; sodium iodide; tetrabutylammomium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone; benzene;

DOI:10.1246/bcsj.59.1887

Reference yield:

(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-carbamoyl-2-azetidinone (84362-43-6) → p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate (85253-98-1,107983-03-9,107983-04-0)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOH / ethanol; H₂O / 1 h / 50 °C

2: ethyl acetate; diethyl ether

3: 78 percent / NaBH₄ / H₂O; tetrahydrofuran / 0.25 h / 0 °C

4: 68 percent / pyridine / tetrahydrofuran; CH₂Cl₂

5: 95 percent / NaI / acetone / 7 h / 60 °C

6: 67 percent / benzene / 10 h / Heating

With pyridine; sodium hydroxide; sodium tetrahydroborate; sodium iodide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone; benzene;

DOI:10.1246/bcsj.59.1887

upstream raw materials:

p-nitrobenzyl glyoxylate

<3S-<3α(S^*),4β>>-3-(1-t-butyldimethylsilyloxyethyl)-4-iodomethyl-2-azetidinone

p-nitrobenzyl glyoxylate monohydrate

benzyl (2S,5R,6R)-6-<(R)-1-hydroxyethyl>penicillanate

Downstream raw materials:

p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-chloroacetate

p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-hydroxyethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

p-nitrobenzyl (2S,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate