(2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-ol
CAS No.:174148-51-7
Molecular Formula:C₂₂H₂₇NO₄
Molecular Weight:369.461
Hs Code.:

Synonyms:(2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

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Chemical Property of (2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

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Technology Process of (2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

There total 8 articles about (2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-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: 73.0%

: 148302-26-5
(3aS,4R,7aS)-1-Benzyl-4-(4-methoxy-benzyloxymethyl)-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

: 174148-51-7
(2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃;
DOI:10.1021/ja952907g

Reference yield:

: 100-39-0
benzyl bromide

: 174148-51-7
(2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH, tetrabutylammonium iodide / 1.) DMF, 2.) DMF, RT

2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

3: 1.) NaH / 1.) DMF, from 0 deg C to RT, 2.) DMF, from 0 deg C to RT

4: 73 percent / LiAlH₄ / diethyl ether / 0 °C

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja952907g

Reference yield:

: 137915-37-8
1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

: 174148-51-7
(2R,3S,4S)-4-(Benzyl-methyl-amino)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, RT, overnight

2: BF₃*Et₂O / CH₂Cl₂ / 5 h / -78 °C

3: 80 percent / TsOH*H₂O, Py / H₂O / 14 h / 80 °C

4: 1.) NaH, tetrabutylammonium iodide / 1.) DMF, 2.) DMF, RT

5: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

6: 1.) NaH / 1.) DMF, from 0 deg C to RT, 2.) DMF, from 0 deg C to RT

7: 73 percent / LiAlH₄ / diethyl ether / 0 °C

With pyridine; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1021/ja952907g