(-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

Base Information

Chemical Name:(-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine
CAS No.:1607004-54-5
Molecular Formula:C₁₆H₂₂N₂O₅S
Molecular Weight:354.427
Hs Code.:

Synonyms:(-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

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Chemical Property of (-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

Chemical Property:

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Technology Process of (-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

There total 5 articles about (-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine 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:

: 1607004-61-4
(+)-(6S)-2,2-bis((tert-butyldimethylsilyloxy)methyl)-6-chloromethyl-4-methylmorpholine

: 1607004-54-5
(-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

: 1607004-55-6
(-)-(2R,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

Guidance literature:: Multi-step reaction with 3 steps

1.1: dimethyl sulfoxide / 24 h / 110 °C

2.1: hydrogenchloride / water / 10 h / 25 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 16 h / -78 - 0 °C

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; water; dimethyl sulfoxide;
DOI:10.1021/jo500609a

Reference yield:

: 1607004-62-5
(-)-(6R)-2,2-bis((tert-butyldimethylsilyloxy)methyl)-6-cyanomethyl-4-methylmorpholine

: 1607004-54-5
(-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

: 1607004-55-6
(-)-(2R,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogenchloride / water / 10 h / 25 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 16 h / -78 - 0 °C

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; water;
DOI:10.1021/jo500609a

Reference yield:

: 1607004-59-0
(-)-(2S)-N-nosylate-2-[1-bromo-2,2-bis((tert-butyldimethylsilyloxy)methyl)ethan-2-yloxy]-3-chloropropan-1-amine

: 1607004-54-5
(-)-(2S,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

: 1607004-55-6
(-)-(2R,6R)-2-hydroxymethyl-2-tosyloxymethyl-6-cyanomethyl-4-methylmorpholine

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium carbonate / acetonitrile / 6 h / Reflux

2.1: lithium hydroxide; 1-thiopropane / acetonitrile / 6 h / 25 °C

3.1: sodium tris(acetoxy)borohydride / water; 1,2-dichloro-ethane / 16 h / 25 °C

4.1: dimethyl sulfoxide / 24 h / 110 °C

5.1: hydrogenchloride / water / 10 h / 25 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 16 h / -78 - 0 °C

With hydrogenchloride; n-butyllithium; 1-thiopropane; sodium tris(acetoxy)borohydride; potassium carbonate; lithium hydroxide; In tetrahydrofuran; hexane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/jo500609a