(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

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Chemical Name:(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline
CAS No.:174873-29-1
Molecular Formula:C₃₈H₅₅N₃O₈Si
Molecular Weight:709.955
Hs Code.:

(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

Synonyms:(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

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Chemical Property of (3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

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Technology Process of (3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

There total 15 articles about (3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline 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: 95.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 174873-28-0
(S)-6-Amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

: 174873-29-1
(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

Guidance literature:: With dmap; In tetrahydrofuran; for 4h; Heating;
DOI:10.1021/ja953777e

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 174873-29-1
(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2: 97 percent / NaH / tetrahydrofuran / 2 h / 0 °C

3: NH₂NH₂, EtOH / 20 h / 140 °C

4: 95 percent / DMAP / tetrahydrofuran / 4 h / Heating

With 2,6-dimethylpyridine; dmap; ethanol; sodium hydride; hydrazine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja953777e

Reference yield:

: 25945-96-4
2-benzyloxy-4-nitro-phenylamine

: 174873-29-1
(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[bis(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / NBS / acetonitrile / 2 h / 25 °C

2: 95 percent / dimethylformamide / 16 h / Heating

3: 100 percent / Al(Hg) / diethyl ether; aq. ethanol / 2 h / 0 - 25 °C

4: 96 percent / K₂CO₃, DMAP / tetrahydrofuran / 16 h / 25 °C

5: 84 percent / Pb(OAc)4 / CHCl₃ / 4 h / 0 - 25 °C

6: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / -20 °C

7: (DHQ)2-PHAL, OsO₄, K₃Fe(CN)6, K₂CO₃, CH₃SO₂NH₂ / tetrahydrofuran; H₂O / 16 h

8: 1.) Bu₂SnO, 2.) Et₃N / 1.) toluene, THF, reflux, 6 h, 2.) 25 deg C, 12 h

9: 73 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

10: 97 percent / NaH / tetrahydrofuran / 2 h / 0 °C

11: NH₂NH₂, EtOH / 20 h / 140 °C

12: 95 percent / DMAP / tetrahydrofuran / 4 h / Heating

With 2,6-dimethylpyridine; lead(IV) acetate; dmap; aluminum amalgam; N-Bromosuccinimide; osmium(VIII) oxide; (DHQ)2-PHAL; ethanol; methanesulfonamide; boron trifluoride diethyl etherate; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); hydrazine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja953777e