methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate

Base Information

Chemical Name:methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate
CAS No.:198978-51-7
Molecular Formula:C₂₂H₂₃NO₆
Molecular Weight:397.428
Hs Code.:

Synonyms:methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate

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Chemical Property of methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate

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Technology Process of methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate

There total 4 articles about methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-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: 86.0%

: 198978-53-9
N-(p-methoxybenzyl)-N'-[(1S)-1-benzyl-1-formyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester

: 198978-51-7
methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate

Guidance literature:: With sulfuric acid; In toluene; for 0.333333h; Heating;
DOI:10.1021/jo9904967

Reference yield:

: 67812-33-3
(4R,5R)-5-(methoxycarbonyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid

: 198978-51-7
methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / bromotripyrrolidinophosphonium hexafluorophosphate; DIPEA / CH₂Cl₂ / 12 h / 25 °C

2: 95 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

3: 86 percent / H₂SO₄*SiO₂ / toluene / 0.33 h / Heating

With oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; toluene; 1: Acylation / 2: Oxidation / 3: Cyclization;
DOI:10.1021/jo9904967

Reference yield:

: 91373-74-9
(2S)-2--3-phenyl-1-propanol

: 198978-51-7
methyl (1R,4S,5S,7R)-3-(p-methoxybenzyl)-2-oxo-4-exo-benzyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / bromotripyrrolidinophosphonium hexafluorophosphate; DIPEA / CH₂Cl₂ / 12 h / 25 °C

2: 95 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

3: 86 percent / H₂SO₄*SiO₂ / toluene / 0.33 h / Heating

With oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; toluene; 1: Acylation / 2: Oxidation / 3: Cyclization;
DOI:10.1021/jo9904967