2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine

Base Information

• Chemical Name: 2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine
• CAS No.: 165545-45-9
• Molecular Formula: C₃₂H₄₂ClNO₃Si
• Molecular Weight: 552.229

Synonyms:2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine

Chemical Property of 2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine

Chemical Property:

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Technology Process of 2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine

There total 14 articles about 2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine 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: 91.0%

{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-acetonitrile (165545-44-8) → 2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine (165545-45-9)

Guidance literature:

With lithium aluminium tetrahydride; sulfuric acid;

DOI:10.1021/ja00135a021

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine (165545-45-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 83 percent / acid

2: pyridine

3: 1.) LDA, 2.) HMPA / 2.) THF, ether, -110 deg C

4: 75 percent / H₂ / Pd/C

5: 100 percent / NMM

6: 67 percent / c-Hex₃SnH, AIBN

7: tributylstannane, AIBN / benzene / Heating

8: LAH / tetrahydrofuran

9: imidazole, DMAP

10: 93 percent / Na(CN)BH₄, TiCl₄

11: pyridine

12: 18-c-6

13: 91 percent / LAH, H₂SO₄

With 4-methyl-morpholine; pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; tricyclohexyltin hydride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); Na(CN)BH₄; sulfuric acid; hydrogen; tri-n-butyl-tin hydride; titanium tetrachloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; benzene;

DOI:10.1021/ja00135a021

Reference yield:

((2S,4R,5R)-5-Benzyloxy-2-phenyl-[1,3]dioxan-4-yl)-methanol (165545-35-7) → 2-{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-ethylamine (165545-45-9)

Guidance literature:

Multi-step reaction with 12 steps

1: pyridine

2: 1.) LDA, 2.) HMPA / 2.) THF, ether, -110 deg C

3: 75 percent / H₂ / Pd/C

4: 100 percent / NMM

5: 67 percent / c-Hex₃SnH, AIBN

6: tributylstannane, AIBN / benzene / Heating

7: LAH / tetrahydrofuran

8: imidazole, DMAP

9: 93 percent / Na(CN)BH₄, TiCl₄

10: pyridine

11: 18-c-6

12: 91 percent / LAH, H₂SO₄

With 4-methyl-morpholine; pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; tricyclohexyltin hydride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); Na(CN)BH₄; sulfuric acid; hydrogen; tri-n-butyl-tin hydride; titanium tetrachloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; benzene;

DOI:10.1021/ja00135a021

upstream raw materials:

{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-acetonitrile

benzaldehyde dimethyl acetal

tert-butylchlorodiphenylsilane

(2S,4R,5R)-2-Phenyl-4-(2,2,2-trichloro-ethyl)-[1,3]dioxan-5-ol

Downstream raw materials:

{2-[(2S,3S,5R,6R)-5-Benzyloxy-3-chloro-6-(2,2-dibromo-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

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