p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

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Chemical Name:p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate
CAS No.:126579-20-2
Molecular Formula:C₂₂H₃₀N₂O₇Si
Molecular Weight:462.575
Hs Code.:

Synonyms:p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

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Chemical Property of p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

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Technology Process of p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 10 articles about p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 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:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 126579-20-2
p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 1) cuprous iodide / 1) THF, -15 deg C, 15 min; 2) THF, 10 min at -30 deg C, then 1 h at 10 deg C

2: 1) potassium tert-butoxide / 1) toluene, 0 deg C, 30 min; 2) toluene, -30 deg C, 20 min

3: 100 percent / osmium tetroxide / dioxane / 20 h / Ambient temperature

4: 87 percent / periodic acid / tetrahydrofuran / 0.5 h / 0 °C

5: 63 percent / 1,1,3,3-tetramethylguanidine / 0.5 h / -20 °C

6: 1) mesyl chloride; 2) Et₃N / 1) CH₂Cl₂, 5 min, 0 deg C; 2) 45 min

7: 1) lithium-hexamethyldisalazane / 1) THF, hexane, -100 deg C; 2) THF, -80 deg C

8: 100 percent / 30percent aq. hydrogen peroxide / CH₂Cl₂ / 0.75 h / 10 °C

9: 1) ozone, MeOH; 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 25 min; 2) 0 deg C, 45 min

With methanol; copper(l) iodide; osmium(VIII) oxide; dimethylsulfide; potassium tert-butylate; dihydrogen peroxide; ozone; methanesulfonyl chloride; periodic acid; triethylamine; lithium hexamethyldisilazane; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo00297a026

Reference yield:

: 80433-47-2
(3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-(prop-2-enyl)-2-azetidinone

: 126579-20-2
p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 1) potassium tert-butoxide / 1) toluene, 0 deg C, 30 min; 2) toluene, -30 deg C, 20 min

2: 100 percent / osmium tetroxide / dioxane / 20 h / Ambient temperature

3: 87 percent / periodic acid / tetrahydrofuran / 0.5 h / 0 °C

4: 63 percent / 1,1,3,3-tetramethylguanidine / 0.5 h / -20 °C

5: 1) mesyl chloride; 2) Et₃N / 1) CH₂Cl₂, 5 min, 0 deg C; 2) 45 min

6: 1) lithium-hexamethyldisalazane / 1) THF, hexane, -100 deg C; 2) THF, -80 deg C

7: 100 percent / 30percent aq. hydrogen peroxide / CH₂Cl₂ / 0.75 h / 10 °C

8: 1) ozone, MeOH; 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 25 min; 2) 0 deg C, 45 min

With methanol; osmium(VIII) oxide; dimethylsulfide; potassium tert-butylate; dihydrogen peroxide; ozone; methanesulfonyl chloride; periodic acid; triethylamine; lithium hexamethyldisilazane; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo00297a026

Reference yield:

: 126579-11-1
p-nitrobenzyl (3S,4R)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-propenyl)-1-azetidineacetate

: 126579-20-2
p-nitrobenzyl (2R,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / osmium tetroxide / dioxane / 20 h / Ambient temperature

2: 87 percent / periodic acid / tetrahydrofuran / 0.5 h / 0 °C

3: 63 percent / 1,1,3,3-tetramethylguanidine / 0.5 h / -20 °C

4: 1) mesyl chloride; 2) Et₃N / 1) CH₂Cl₂, 5 min, 0 deg C; 2) 45 min

5: 1) lithium-hexamethyldisalazane / 1) THF, hexane, -100 deg C; 2) THF, -80 deg C

6: 100 percent / 30percent aq. hydrogen peroxide / CH₂Cl₂ / 0.75 h / 10 °C

7: 1) ozone, MeOH; 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 25 min; 2) 0 deg C, 45 min

With methanol; osmium(VIII) oxide; dimethylsulfide; dihydrogen peroxide; ozone; methanesulfonyl chloride; periodic acid; triethylamine; lithium hexamethyldisilazane; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo00297a026