(2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol

Base Information

Chemical Name:(2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol
CAS No.:1606140-80-0
Molecular Formula:C₂₁H₂₇NO₃
Molecular Weight:341.45
Hs Code.:

Synonyms:(2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol

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Chemical Property of (2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol

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Technology Process of (2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol

There total 3 articles about (2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-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:

: 67-56-1
methanol

: (2R,3R)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentane-1,2-diol

: 1606140-80-0
(2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol

: 1606140-81-1
(2R,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol

Guidance literature:: With hydrogenchloride; at 50 ℃; for 16h; Overall yield = 94 %; diastereoselective reaction;
DOI:10.1016/j.tet.2014.03.055

Reference yield:

: 1606140-68-4
tert-butyl (E)-5,5-diethoxypent-2-enoate

: 1606140-80-0
(2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

1.3: 12 h / -78 - 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / 16 h / 50 °C

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; hexane;
DOI:10.1016/j.tet.2014.03.055

Reference yield:

: 1606140-72-0
tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

: 1606140-80-0
(2S,4R,5R)-2-methoxy-4-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydro-2H-pyran-5-ol

Guidance literature:: Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

2: hydrogenchloride / 16 h / 50 °C

With hydrogenchloride; lithium aluminium tetrahydride; In tetrahydrofuran;
DOI:10.1016/j.tet.2014.03.055