(1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Base Information

Chemical Name:(1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol
CAS No.:954502-27-3
Molecular Formula:C₁₆H₂₃NO₄
Molecular Weight:293.363
Hs Code.:

Synonyms:(1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

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Chemical Property of (1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

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Technology Process of (1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

There total 3 articles about (1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol 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: 97.0%

: 444307-98-6
(1S,5R,8S)-2-benzyl-8-(hydroxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

: 954502-27-3
(1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/chem.200900996

Reference yield:

: 444307-98-6
(1S,5R,8S)-2-benzyl-8-(hydroxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

: 954502-27-3
(1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

: (4aR,7aS,7bS)-7-benzyl-7b-hydroxy-4,4-dimethylhexahydro-2H,4H-1,3,6-trioxa-7-azacyclopenta[cd]indene

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 4.5h; Inert atmosphere;
DOI:10.1055/s-0034-1380571

Reference yield:

: 444307-95-3
(3S,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-[2-(trimethylsilyl)ethoxy]-3,6-dihydro-2H-1,2-oxazine

: 954502-27-3
(1R,5S,8S,9S)-2-benzyl-8-hydroxymethyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

: (4aR,7aS,7bS)-7-benzyl-7b-hydroxy-4,4-dimethylhexahydro-2H,4H-1,3,6-trioxa-7-azacyclopenta[cd]indene

Guidance literature:: Multi-step reaction with 2 steps

1: tin(IV) chloride / acetonitrile / 7 h / -30 - 20 °C / Inert atmosphere

2: sodium tetrahydroborate / ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; tin(IV) chloride; In ethanol; acetonitrile;
DOI:10.1055/s-0034-1380571