(3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one

Base Information

Chemical Name:(3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one
CAS No.:1417339-12-8
Molecular Formula:C₂₂H₂₄FNO₄
Molecular Weight:385.435
Hs Code.:

Synonyms:(3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one

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Chemical Property of (3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one

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Technology Process of (3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one

There total 7 articles about (3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one 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: 43.0%

: 1417339-11-7
((3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-2-oxooctahydrobenzo[d]oxazol-6-yl)methyl methanesulfonate

: 1417339-12-8
(3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one

Guidance literature:: With tetrabutyl ammonium fluoride; In acetonitrile; for 4h; Inert atmosphere; Reflux;

Reference yield:

: 1349172-44-6
(3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-hexahydrobenzo[d]oxazol-2(3H)-one

: 1417339-12-8
(3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: acetic acid; acetic anhydride; zinc(II) chloride / 3 h / 20 °C

1.2: 2 h / 20 °C

2.1: pyridine / 4 h / -20 - 20 °C

3.1: tetrabutyl ammonium fluoride / acetonitrile / 4 h / Inert atmosphere; Reflux

With pyridine; tetrabutyl ammonium fluoride; acetic anhydride; acetic acid; zinc(II) chloride; In acetonitrile;

Reference yield:

: 130970-85-3
rac-((((1R,2R,6R)-6-((benzyloxy)methyl)cyclohex-3-ene-1,2-diyl)bis-(oxy))bis(methylene))dibenzene

: 1417339-12-8
(3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: water; N-Bromosuccinimide / dimethyl sulfoxide; water / 2.5 h / 0 - 20 °C

2.1: dichloromethane / 1.5 h / 0 - 20 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 21.5 h / 0 °C / Reflux

4.1: Chiralpak IA / hexane; ethanol / Resolution of racemate

5.1: acetic acid; acetic anhydride; zinc(II) chloride / 3 h / 20 °C

5.2: 2 h / 20 °C

6.1: pyridine / 4 h / -20 - 20 °C

7.1: tetrabutyl ammonium fluoride / acetonitrile / 4 h / Inert atmosphere; Reflux

With pyridine; N-Bromosuccinimide; tetrabutyl ammonium fluoride; water; acetic anhydride; sodium hydride; acetic acid; zinc(II) chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; mineral oil;