{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile

Base Information

Chemical Name:{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile
CAS No.:850404-95-4
Molecular Formula:C₂₈H₃₉NO₄Si
Molecular Weight:481.707
Hs Code.:

Synonyms:{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile

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Chemical Property of {(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile

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Technology Process of {(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile

There total 9 articles about {(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile 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: 90.0%

: 850404-94-3
{(2S,4S,6R)-6-[(R)-4-benzyloxy-2-methoxybutyl]-4-(tert-butyldiphenylsilanyloxy)tetrahydro-2H-pyran-2-yl}acetonitrile

: 850404-95-4
{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile

Guidance literature:: With boron trichloride; In hexane; dichloromethane; at -78 ℃; for 20h;
DOI:10.1002/anie.200462408

Reference yield:

: 850404-93-2
{(2S,4S,6S)-6-[(R)-4-benzyloxy-2-methoxybutyl]-4-hydroxytetrahydro-2H-pyran-2-yl}acetonitrile

: 850404-95-4
{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide / 72 h

2: 90 percent / BCl₃ / hexane; CH₂Cl₂ / 20 h / -78 °C

With 1H-imidazole; boron trichloride; In hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0610412

Reference yield:

: 850404-89-6
(2S,3S)-2,4,6-trimethylbenzenesulfonic acid 3-(dimethylphenylsilanyl)-2-(trimethylsilanyloxy)pent-4-enyl ester

: 850404-95-4
{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / TfOH / CH₂Cl₂ / 12 h / -78 °C

2.1: 87 percent / dimethylformamide / 60 h / 60 °C

3.1: mercury trifluoroacetate / tetrahydrofuran / 18 h

3.2: 76 percent / NaBH₄; NaOH / tetrahydrofuran

4.1: 95 percent / imidazole / dimethylformamide / 72 h

5.1: 90 percent / BCl₃ / hexane; CH₂Cl₂ / 20 h / -78 °C

With 1H-imidazole; trifluorormethanesulfonic acid; mercury(II) trifluoroacetate; boron trichloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0610412