(3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole

Base Information

Chemical Name:(3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole
CAS No.:1349172-68-4
Molecular Formula:C₃₃H₃₈N₂O₄
Molecular Weight:526.676
Hs Code.:

Synonyms:(3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole

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Chemical Property of (3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole

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Technology Process of (3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole

There total 5 articles about (3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole 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: 21.0%

: 123-75-1
pyrrolidine

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

: 1349172-68-4
(3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole

Guidance literature:: (3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-hexahydrobenzo[d]oxazol-2(3H)-one; With trimethoxonium tetrafluoroborate; In dichloromethane; at 20 ℃; for 24h; Molecular sieve; Inert atmosphere;

pyrrolidine; With triethylamine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 24h;

Reference yield:

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

: 1349172-68-4
(3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole

Guidance literature:: Multi-step reaction with 2 steps

1.1: Chiralpak IA column / hexane; ethanol

2.1: trimethoxonium tetrafluoroborate / dichloromethane / 24 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 24 h / 20 °C

With trimethoxonium tetrafluoroborate; In ethanol; hexane; dichloromethane;

Reference yield:

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

: 1349172-68-4
(3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 2.5 h / 10 - 20 °C

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

3.1: sodium hydride / tetrahydrofuran / 21.5 h / 20 °C / Reflux

4.1: Chiralpak IA column / hexane; ethanol

5.1: trimethoxonium tetrafluoroborate / dichloromethane / 24 h / 20 °C / Molecular sieve; Inert atmosphere

5.2: 24 h / 20 °C

With N-Bromosuccinimide; water; trimethoxonium tetrafluoroborate; sodium hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide;