(4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one

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Chemical Name:(4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one
CAS No.:339046-93-4
Molecular Formula:C₃₆H₄₂N₄O₃Si
Molecular Weight:606.84
Hs Code.:

Synonyms:(4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one

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Chemical Property of (4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one

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Technology Process of (4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one

There total 12 articles about (4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one 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: 85.0%

: (4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-ol

: 339046-93-4
(4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 1.5h;
DOI:10.1021/ja004325r

Reference yield:

: 339046-98-9
(2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide

: 339046-93-4
(4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / xylene / 12 h / Heating

2.1: 3.2 g / diisobutylaluminum hydride / tetrahydrofuran; hexane / 5 h / -78 °C

3.1: 2.54 g / KHMDS / toluene; tetrahydrofuran / 0 - 20 °C

4.1: 95 percent / Ph₃P; DEAD; (PhO)2P(O)N₃ / tetrahydrofuran / 24 h

5.1: 78 percent / aq. HCl / tetrahydrofuran; CH₂Cl₂ / 8 h / 20 °C

6.1: LDA / tetrahydrofuran / 0.5 h / -78 - 0 °C

6.2: 72 percent / tetrahydrofuran / 0.58 h / -78 - 0 °C

7.1: 85 percent / DMSO; (ClCO)2; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With hydrogenchloride; oxalyl dichloride; diphenyl phosphoryl azide; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; toluene; xylene; 3.1: Wittig reaction / 7.1: Swern oxidation;
DOI:10.1021/ja004325r

Reference yield:

: 339046-87-6
3-(tert-butyl-dimethyl-silanyloxymethyl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pent-4-enoic acid diethylamide

: 339046-93-4
(4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 93 percent / PPTS / ethanol / 20 °C

2.1: 97 percent / xylene / 12 h / Heating

3.1: 3.2 g / diisobutylaluminum hydride / tetrahydrofuran; hexane / 5 h / -78 °C

4.1: 2.54 g / KHMDS / toluene; tetrahydrofuran / 0 - 20 °C

5.1: 95 percent / Ph₃P; DEAD; (PhO)2P(O)N₃ / tetrahydrofuran / 24 h

6.1: 78 percent / aq. HCl / tetrahydrofuran; CH₂Cl₂ / 8 h / 20 °C

7.1: LDA / tetrahydrofuran / 0.5 h / -78 - 0 °C

7.2: 72 percent / tetrahydrofuran / 0.58 h / -78 - 0 °C

8.1: 85 percent / DMSO; (ClCO)2; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With hydrogenchloride; oxalyl dichloride; diphenyl phosphoryl azide; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; xylene; 4.1: Wittig reaction / 8.1: Swern oxidation;
DOI:10.1021/ja004325r