(2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-ol

Base Information

Chemical Name:(2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-ol
CAS No.:400009-30-5
Molecular Formula:C₃₃H₃₇NO₄
Molecular Weight:511.661
Hs Code.:

Synonyms:(2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-ol

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Technology Process of (2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-ol

There total 10 articles about (2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-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: 80.0%

: (2`R,3`S,4R,4`R)-3-(2`-benzyloxy-4`-N,N-dibenzylamino-3`-hydroxy-5`-(4``-methoxy-phenyl)-1`-oxopentyl)-4-phenylmethyloxazolidin-2-one

: 400009-30-5
(2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-ol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; methanol; at 20 ℃; for 18h;
DOI:10.1021/ol017016u

Reference yield:

: 556-02-5,18875-48-4,25619-78-7,30704-25-7
tyrosine

: 400009-30-5
(2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / AcCl

2.1: 99 percent / NaHCO₃ / ethanol

3.1: 97 percent / K₂CO₃ / dimethylformamide

4.1: 100 percent / TFA / CH₂Cl₂

5.1: 95 percent / K₂CO₃ / acetonitrile

6.1: 87 percent / LiBH₄ / methanol

7.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

7.2: 75 percent / CH₂Cl₂ / 5 h / -78 - 0 °C

8.1: 80 percent / LiBH₄ / methanol; tetrahydrofuran / 18 h / 20 °C

With lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; sodium hydrogencarbonate; potassium carbonate; triethylamine; acetyl chloride; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 7.1: Swern oxidation;
DOI:10.1021/ol017016u

Reference yield:

: 100-39-0
benzyl bromide

: 400009-30-5
(2S,3S,4R)-benzyloxy-4-N,N-dibenzylamino-3-hydroxy-5-(4'-methoxy-phenyl)pentan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / K₂CO₃ / acetonitrile

2.1: 87 percent / LiBH₄ / methanol

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

3.2: 75 percent / CH₂Cl₂ / 5 h / -78 - 0 °C

4.1: 80 percent / LiBH₄ / methanol; tetrahydrofuran / 18 h / 20 °C

With lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 3.1: Swern oxidation;
DOI:10.1021/ol017016u