[(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane
CAS No.:516457-38-8
Molecular Formula:C₂₁H₃₅BrO₄Si
Molecular Weight:459.496
Hs Code.:

Synonyms:[(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane

There total 11 articles about [(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane 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:

: Toluene-4-sulfonic acid 2-[(2S,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethyl ester

: 516457-38-8
[(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With lithium bromide; In N,N-dimethyl-formamide;
DOI:10.1021/ol0341804

Reference yield:

: 118620-86-3,132437-17-3
(2S,3S)-4-(p-methoxybenzyloxy)-2,3-(isopropylidenedioxy)-butan-1-ol

: 516457-38-8
[(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 11 steps

1: pyridine

2: NaI; CaCO₃ / acetone

3: 87 percent / n-BuLi / tetrahydrofuran; hexane

4: 58 percent / conc. HCl

5: 99 percent / 1 M HCl / H₂O; tetrahydrofuran

6: acetonitrile

7: NaOMe / methanol

8: 42 percent / imidazole

9: 100 percent / LiAlH₄ / tetrahydrofuran

10: pyridine

11: LiBr / dimethylformamide

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; sodium methylate; calcium carbonate; sodium iodide; lithium bromide; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 6: Wittig reaction;
DOI:10.1021/ol0341804

Reference yield:

: Toluene-4-sulfonic acid (4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 516457-38-8
[(2S,3S,5R)-5-(2-Bromo-ethyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 10 steps

1: NaI; CaCO₃ / acetone

2: 87 percent / n-BuLi / tetrahydrofuran; hexane

3: 58 percent / conc. HCl

4: 99 percent / 1 M HCl / H₂O; tetrahydrofuran

5: acetonitrile

6: NaOMe / methanol

7: 42 percent / imidazole

8: 100 percent / LiAlH₄ / tetrahydrofuran

9: pyridine

10: LiBr / dimethylformamide

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; sodium methylate; calcium carbonate; sodium iodide; lithium bromide; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 5: Wittig reaction;
DOI:10.1021/ol0341804