(1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

Base Information

Chemical Name:(1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate
CAS No.:869385-11-5
Molecular Formula:C₄₉H₆₉NO₈Si
Molecular Weight:828.174
Hs Code.:

(1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

Synonyms:(1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

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Chemical Property of (1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

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Technology Process of (1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

There total 16 articles about (1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate 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: 57.0%

: 869385-07-9
(12R,13S,E)-tert-butyl 12-benzyloxy-2,2,13,23,23-pentamethyl-9,15,21-trioxo-3,3-diphenyl-4,22-dioxa-20-aza-3-silatetracos-10-ene-16-carboxylate

: 869385-11-5
(1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

: (1S,2R,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

Guidance literature:: With caesium carbonate; In ethanol; at -78 - 0 ℃;
DOI:10.1002/anie.200502296

Reference yield:

: 869385-07-9
(12R,13S,E)-tert-butyl 12-benzyloxy-2,2,13,23,23-pentamethyl-9,15,21-trioxo-3,3-diphenyl-4,22-dioxa-20-aza-3-silatetracos-10-ene-16-carboxylate

: 869385-11-5
(1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

: (1S,2R,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

: (1R,2R,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

Guidance literature:: With lithium methanolate; lithium perchlorate; In diethyl ether; at 0 ℃;
DOI:10.1002/anie.200502296

Reference yield:

: (3S,4R)-4-Benzyloxy-3-methyl-5-oxo-pentanenitrile

: 869385-11-5
(1S,2S,3R,4S)-tert-butyl 3-benzyloxy-1-(3-(tert-butoxycarbonylamino)propyl)-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 7.1 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C

2.1: L-selectride / tetrahydrofuran / 1.5 h / -78 °C

3.1: 5.25 g / imidazole / dimethylformamide / 30 h / 20 °C

4.1: 83 percent / Dibal-H / CH₂Cl₂ / 1.5 h / -78 - -50 °C

5.1: LDA / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

6.1: PPTS / ethanol / 2.5 h / 20 °C

6.2: 301 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 20 °C

7.1: 57 percent / Cs₂CO₃ / ethanol / -78 - 0 °C

With 1H-imidazole; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; diisobutylaluminium hydride; caesium carbonate; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Horner-Wadsworth-Emmons reaction / 6.2: Dess-Martin oxidation / 7.1: Michael reaction;
DOI:10.1002/anie.200502296