[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

Base Information

Chemical Name:[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester
CAS No.:516457-47-9
Molecular Formula:C₂₂H₃₆O₆Si
Molecular Weight:424.61
Hs Code.:

Synonyms:[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

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Chemical Property of [(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

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Technology Process of [(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

There total 8 articles about [(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester 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: 42.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: [(4S,5S)-4-Hydroxy-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

: 516457-47-9
[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

: [(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

Guidance literature:: With 1H-imidazole;
DOI:10.1021/ol0341804

Reference yield:

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

: 516457-47-9
[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 1H-imidazole; hydrogenchloride; n-butyllithium; sodium methylate; calcium carbonate; sodium iodide; In tetrahydrofuran; methanol; hexane; water; 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

: 516457-47-9
[(2R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; hydrogenchloride; n-butyllithium; sodium methylate; calcium carbonate; sodium iodide; In tetrahydrofuran; methanol; hexane; water; acetone; acetonitrile; 5: Wittig reaction;
DOI:10.1021/ol0341804