(1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

Base Information

Chemical Name:(1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione
CAS No.:194852-21-6
Molecular Formula:C₂₁H₂₈N₆O₇
Molecular Weight:476.489
Hs Code.:

Synonyms:(1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

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Chemical Property of (1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

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Technology Process of (1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

There total 1 articles about (1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione 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: 33.0%

: 63777-16-2
dihydrobicyclomycin 2',3'-acetonide

: 4-Azidoaniline hydrochloride

: 194852-21-6
(1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

Guidance literature:: With sodium hydroxide; In methanol; water; for 24h; Ambient temperature;
DOI:10.1021/jo970575n

Reference yield: 76.0%

: 194852-21-6
(1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

: (1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-((1S,2S)-1,2,3-trihydroxy-2-methyl-propyl)-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

Guidance literature:: With trifluoroacetic acid; In methanol; water; for 2h; Ambient temperature;
DOI:10.1021/jo970575n

Reference yield:

: 194852-21-6
(1S,6R)-5-[(4-Azido-phenylamino)-methyl]-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

: 3-Formyl-benzoic acid (1S,5R,6R)-6-hydroxy-8,10-dioxo-1-((1S,2S)-1,2,3-trihydroxy-2-methyl-propyl)-2-oxa-7,9-diaza-bicyclo[4.2.2]dec-5-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: O₃

2: H₂ / Pd/C

3: 43 percent / DCC, TEA, DMAP / tetrahydrofuran / 3 h / Ambient temperature

4: 43 percent / TFA / methanol; H₂O / 2 h / Ambient temperature

With dmap; TEA; hydrogen; ozone; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo970575n