(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane

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Chemical Name:(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane
CAS No.:857685-66-6
Molecular Formula:C₃₀H₅₁NO₄S₂Si
Molecular Weight:581.957
Hs Code.:

Synonyms:(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane

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Chemical Property of (1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane

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Technology Process of (1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane

There total 12 articles about (1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane 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: 99.0%

: 857685-65-5
1-(R)-(2'-benzyloxy-1'-(R)-methyl-ethyl)-2-(S)-(3''-iodo-propyl)-2-(S)-nitro-cyclopentane

: 74739-24-5
tert-Butyl-(2-[1,3]dithian-2-yl-ethoxy)-dimethyl-silane

: 857685-66-6
(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane

Guidance literature:: 1-(R)-(2'-benzyloxy-1'-(R)-methyl-ethyl)-2-(S)-(3''-iodo-propyl)-2-(S)-nitro-cyclopentane; With N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;

tert-Butyl-(2-[1,3]dithian-2-yl-ethoxy)-dimethyl-silane; In tetrahydrofuran; at -78 ℃; for 0.666667h;
DOI:10.1021/jo047882v

Reference yield:

: 4934-95-6
methyl 2-(2-oxocyclopentyl)acetate

: 857685-66-6
(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane

Guidance literature:: Multi-step reaction with 12 steps

1.1: hydrogen / [(R)-BINAP-RuCl₂](DMF)n / methanol / 24 h / 100 °C / 19001.3 Torr

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: tetrahydrofuran; hexane / 6 h / -78 °C

3.1: LiAlH₄ / tetrahydrofuran / 4 h / Heating

4.1: sodium hydride / tetrahydrofuran / 10 h / 20 °C

5.1: pyridinium chlorochromate; Celite / CH₂Cl₂ / 4 h / 20 °C

6.1: hydroxylamine hydrochloride; potassium carbonate / methanol / 4 h / 20 °C

7.1: m-CPBA; Na₂HPO₄; urea / acetonitrile / 80 °C

8.1: Triton B / methanol; tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 20 °C

9.1: LiBH₄ / tetrahydrofuran / 24 h / 20 °C

10.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

11.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

12.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

12.2: tetrahydrofuran; pentane / 3 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; lithium borohydride; Celite; hydroxylamine hydrochloride; hydrogen; tert.-butyl lithium; N-benzyl-trimethylammonium hydroxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; urea; pyridinium chlorochromate; sodium iodide; lithium diisopropyl amide; [(R)-BINAP-RuCl₂](DMF)n; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; acetonitrile; tert-butyl alcohol; pentane; 8.1: Michael addition;
DOI:10.1016/j.tet.2007.03.031

Reference yield:

: 857685-64-4
(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-(3-hydroxypropyl)-2-nitro-cyclopentane

: 857685-66-6
(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitro-2-[3-(2-{2-[(tert-butyl)dimethylsilanyloxy]ethyl}-1,3-dithian-2-yl)propyl]-cyclopentane

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

3.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.2: tetrahydrofuran; pentane / 3 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tert.-butyl lithium; sodium hydrogencarbonate; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; acetone; pentane;
DOI:10.1016/j.tet.2007.03.031