(R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

Base Information

Chemical Name:(R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol
CAS No.:1293280-11-1
Molecular Formula:C₂₀H₃₁NO₅
Molecular Weight:365.47
Hs Code.:

Synonyms:(R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

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Chemical Property of (R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

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Technology Process of (R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

There total 7 articles about (R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol 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: 24.6%

: 1293280-09-7
((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)carboxaldehyde

: 75-16-1
methylmagnesium bromide

: 1293280-12-2
(S)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

: 1293280-11-1
(R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

Guidance literature:: ((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)carboxaldehyde; methylmagnesium bromide; In tetrahydrofuran; toluene; at 20 ℃;

With ammonium chloride; In tetrahydrofuran; toluene;

Reference yield: 24.6%

: 1293280-09-7
((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)carboxaldehyde

: 75-16-1
methylmagnesium bromide

: 1293280-11-1
(R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

: (S)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

Guidance literature:: In tetrahydrofuran; toluene; at 20 ℃;

Reference yield:

: 1084896-40-1
(2S,3S,4aS,5S,8R,8aR)-5-(benzyloxy)-2,3-dimethoxy-2,3-dimethylhexahydro-2H-pyrano[3,4-b][1,4]dioxine-8-carbonitrile

: 1293280-12-2
(S)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

: 1293280-11-1
(R)-1-((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridin-8-yl)ethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: ammonium formate / palladium(II) hydroxide / methanol / 24 h / 50 - 55 °C

1.2: Cooling with ice

2.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 40 °C

2.2: 40 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

3.2: Cooling

4.1: toluene; tetrahydrofuran / 20 °C

With oxalyl dichloride; ammonium formate; potassium carbonate; dimethyl sulfoxide; palladium(II) hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Swern Oxidation / 3.2: Swern Oxidation;