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

Base Information

Chemical Name:{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-methanol
CAS No.:165545-43-7
Molecular Formula:C₃₁H₃₉ClO₄Si
Molecular Weight:539.187
Hs Code.:

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

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

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

There total 11 articles about {(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-methanol 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: 93.0%

: 165545-42-6
tert-Butyl-[2-((2S,4aR,6S,7S,8aR)-7-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethoxy]-diphenyl-silane

: 165545-43-7
{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-methanol

Guidance literature:: With Na(CN)BH₄; titanium tetrachloride;
DOI:10.1021/ja00135a021

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 165545-43-7
{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-methanol

Guidance literature:: Multi-step reaction with 10 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

With 4-methyl-morpholine; pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; tricyclohexyltin hydride; 2,2'-azobis(isobutyronitrile); Na(CN)BH₄; hydrogen; tri-n-butyl-tin hydride; titanium tetrachloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; benzene;
DOI:10.1021/ja00135a021

Reference yield:

: 165545-35-7
((2S,4R,5R)-5-Benzyloxy-2-phenyl-[1,3]dioxan-4-yl)-methanol

: 165545-43-7
{(2R,3R,5S,6S)-3-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-tetrahydro-pyran-2-yl}-methanol

Guidance literature:: Multi-step reaction with 9 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

With 4-methyl-morpholine; pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; tricyclohexyltin hydride; 2,2'-azobis(isobutyronitrile); Na(CN)BH₄; hydrogen; tri-n-butyl-tin hydride; titanium tetrachloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; benzene;
DOI:10.1021/ja00135a021