(5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane

Base Information

Chemical Name:(5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane
CAS No.:88669-90-3
Molecular Formula:C₁₈H₁₈N₆O₈
Molecular Weight:446.376
Hs Code.:

Synonyms:(5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane

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Chemical Property of (5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane

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Technology Process of (5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane

There total 8 articles about (5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane 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: 89.0%

: 88669-87-8
(3S,4R)-3-<(R)-1-hydroxyethyl>-4-<2-oxo-3-diazo-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)propyl>azetidin-2-one

: 88669-90-3
(5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane

Guidance literature:: With dirhodium tetraacetate; In dichloromethane; for 1h; Heating;
DOI:10.1021/ja00318a042

Reference yield:

: 50780-46-6
((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl chloride

: 88669-90-3
(5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane

Guidance literature:: Multi-step reaction with 6 steps

1: 37 percent / triethylamine / acetonitrile / 1.) r.t., 16 h; 2.) 60 deg C, 1 h

2: 1.) lithium triethylcarboxide / 1.) THF, hexane, -78 deg C, 10 min; 2.) dichloromethane, dimethylformamide, -78 deg C, 45 min

3: trifluoroacetic acid / CH₂Cl₂ / 6 h / Ambient temperature

4: 0.72 g / hydrofluoric acid / acetonitrile / 18 h / -10 °C

5: 0.302 g / p-dodecylbenzenesulfonylazide, triethylamine / hexane; CH₂Cl₂ / 1 h / -15 °C

6: 89 percent / rhodium acetate dimer / CH₂Cl₂ / 1 h / Heating

With dirhodium tetraacetate; hydrogen fluoride; lithium 3-ethylpentan-3-olate; 4-dodecylbenzenesulphonyl azide; triethylamine; trifluoroacetic acid; In hexane; dichloromethane; acetonitrile;
DOI:10.1021/ja00318a042

Reference yield:

: 88670-04-6
(3S,4R)-1-tert-butyldimethylsilyl-3-<(R)-2-((tert-butyldimethylsilyl)oxy)ethyl>-2-oxo-azetidin-4-acetic acid

: 88669-90-3
(5R,6S)-3,7-dioxo-6-<(R)-1-hydroxyethyl>-2-(1-(((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl)tetrazol-5-yl)-1-azabicyclo<3.2.0>heptane

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) sodium carbonate; 2.) oxalyl chloride / 1.) THF, acetonitrile, 50 deg C, 1 h; 2.) dichloromethane, dimethylformamide, -15 deg C

2: 1.) lithium triethylcarboxide / 1.) THF, hexane, -78 deg C, 10 min; 2.) dichloromethane, dimethylformamide, -78 deg C, 45 min

3: trifluoroacetic acid / CH₂Cl₂ / 6 h / Ambient temperature

4: 0.72 g / hydrofluoric acid / acetonitrile / 18 h / -10 °C

5: 0.302 g / p-dodecylbenzenesulfonylazide, triethylamine / hexane; CH₂Cl₂ / 1 h / -15 °C

6: 89 percent / rhodium acetate dimer / CH₂Cl₂ / 1 h / Heating

With dirhodium tetraacetate; oxalyl dichloride; hydrogen fluoride; lithium 3-ethylpentan-3-olate; sodium carbonate; 4-dodecylbenzenesulphonyl azide; triethylamine; trifluoroacetic acid; In hexane; dichloromethane; acetonitrile;
DOI:10.1021/ja00318a042