{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

Base Information

Chemical Name:{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile
CAS No.:850404-98-7
Molecular Formula:C₃₄H₄₇NO₅Si
Molecular Weight:577.836
Hs Code.:

{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

Synonyms:{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

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Chemical Property of {(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

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Technology Process of {(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

There total 17 articles about {(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]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: 93.0%

: 850404-97-6
(2S,5S,6R)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyltetrahydro-2H-pyran-2-carboxylic acid isopropyl ester

: 850404-98-7
{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃; for 1h;
DOI:10.1002/anie.200462408 DOI:10.1021/jo0610412

Reference yield:

: 850405-00-4
(2S,3S)-3-(Dimethyl-phenyl-silanyl)-pent-4-ene-1,2-diol

: 850404-98-7
{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

Guidance literature:: Multi-step reaction with 11 steps

1.1: 89 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 72 h / 20 °C

2.1: 92 percent / pyridine / tetrahydrofuran / 12 h

3.1: 80 percent / TfOH / CH₂Cl₂ / 12 h / -78 °C

4.1: 87 percent / dimethylformamide / 60 h / 60 °C

5.1: mercury trifluoroacetate / tetrahydrofuran / 18 h

5.2: 76 percent / NaBH₄; NaOH / tetrahydrofuran

6.1: 95 percent / imidazole / dimethylformamide / 72 h

7.1: 90 percent / BCl₃ / hexane; CH₂Cl₂ / 20 h / -78 °C

8.1: 85 percent / pyridinium chlorochromate; molecular sieves / CH₂Cl₂ / 2 h

9.1: 73 percent / trimethylsilyl triflate / CH₂Cl₂ / 12 h / -50 °C

10.1: 89 percent / hydrogen / Pd/C / ethyl acetate / 18 h

11.1: 93 percent / DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

With pyridine; 1H-imidazole; dmap; molecular sieve; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; hydrogen; mercury(II) trifluoroacetate; boron trichloride; diisobutylaluminium hydride; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo0610412

Reference yield:

: 850404-92-1
{(2S,6S)-6-[(R)-4-benzyloxy-2-methoxybutyl]-5,6-dihydro-2H-pyran-2-yl}acetonitrile

: 850404-98-7
{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: mercury trifluoroacetate / tetrahydrofuran / 18 h

1.2: 76 percent / NaBH₄; NaOH / tetrahydrofuran

2.1: 95 percent / imidazole / dimethylformamide / 72 h

3.1: 90 percent / BCl₃ / hexane; CH₂Cl₂ / 20 h / -78 °C

4.1: 85 percent / pyridinium chlorochromate; molecular sieves / CH₂Cl₂ / 2 h

5.1: 73 percent / trimethylsilyl triflate / CH₂Cl₂ / 12 h / -50 °C

6.1: 89 percent / hydrogen / Pd/C / ethyl acetate / 18 h

7.1: 93 percent / DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

With 1H-imidazole; molecular sieve; trimethylsilyl trifluoromethanesulfonate; hydrogen; mercury(II) trifluoroacetate; boron trichloride; diisobutylaluminium hydride; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo0610412