4,6-Dioxa-2-azabicyclo[3.3.1]non-2-ene-5-carboxylic acid, 8-(acetylamino)-3-phenyl-7-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-, methyl ester, (1S,5S,7R,8R)-

Base Information

Chemical Name:4,6-Dioxa-2-azabicyclo[3.3.1]non-2-ene-5-carboxylic acid, 8-(acetylamino)-3-phenyl-7-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-, methyl ester, (1S,5S,7R,8R)-
CAS No.:392712-45-7
Molecular Formula:C25H30N2O11
Molecular Weight:534.52
Hs Code.:
Mol file:392712-45-7.mol

4,6-Dioxa-2-azabicyclo[3.3.1]non-2-ene-5-carboxylic acid,
8-(acetylamino)-3-phenyl-7-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-, methyl
ester, (1S,5S,7R,8R)-

Synonyms:

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Chemical Property of 4,6-Dioxa-2-azabicyclo[3.3.1]non-2-ene-5-carboxylic acid, 8-(acetylamino)-3-phenyl-7-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-, methyl ester, (1S,5S,7R,8R)-

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Technology Process of 4,6-Dioxa-2-azabicyclo[3.3.1]non-2-ene-5-carboxylic acid, 8-(acetylamino)-3-phenyl-7-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-, methyl ester, (1S,5S,7R,8R)-

There total 4 articles about 4,6-Dioxa-2-azabicyclo[3.3.1]non-2-ene-5-carboxylic acid, 8-(acetylamino)-3-phenyl-7-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-, methyl ester, (1S,5S,7R,8R)- 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: 96.0%

: 392712-43-5
(1R,5R,7R,8R,9S)-8-Acetylamino-9-bromo-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

: 392712-45-7
(1S,5S,7R,8R)-8-Acetylamino-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; for 2h; Heating;
DOI:10.1081/CAR-100105710

Reference yield:

: 93-97-0
benzoic acid anhydride

: 392712-45-7
(1S,5S,7R,8R)-8-Acetylamino-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / DMAP / pyridine / 20 °C

2: 84 percent / N-bromosuccinimide / acetonitrile; H₂O / 0.5 h / 80 °C

3: 96 percent / n-Bu₃SnH; AIBN / tetrahydrofuran / 2 h / Heating

With dmap; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; pyridine; water; acetonitrile;
DOI:10.1081/CAR-100105710

Reference yield:

: 139110-70-6
5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester

: 392712-45-7
(1S,5S,7R,8R)-8-Acetylamino-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / DMAP / pyridine / 20 °C

2: 84 percent / N-bromosuccinimide / acetonitrile; H₂O / 0.5 h / 80 °C

3: 96 percent / n-Bu₃SnH; AIBN / tetrahydrofuran / 2 h / Heating

With dmap; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; pyridine; water; acetonitrile;
DOI:10.1081/CAR-100105710