1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose

Base Information

Chemical Name:1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose
CAS No.:204588-85-2
Molecular Formula:C₂₃H₂₇F₃O₁₁S
Molecular Weight:568.522
Hs Code.:

Synonyms:1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose

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Chemical Property of 1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose

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Technology Process of 1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose

There total 1 articles about 1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose 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:

: 22009-38-7
7-hydroxy-1-tetralone

: 204588-85-2
1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / imidazole / dimethylformamide / 20 °C

2: 77 percent / sodium borohydride / methanol / 1 h

3: 73 percent / tetraethylammonium bromide; 4 Angstroem molecular sieves / CH₂Cl₂ / 24 h / 20 °C

4: H₂ / Pd-C / ethanol

5: 0.72 g / pyridine; DMAP / 24 h

6: TBAF / tetrahydrofuran / 0.5 h / 0 °C

7: 0.54 g / 2,6-lutidine; DMAP / CH₂Cl₂ / 24 h / -20 - 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; 4 A molecular sieve; tetraethylammonium bromide; tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Reduction / 3: Condensation / 4: Hydrogenolysis / 5: Acetylation / 6: desilylation / 7: Esterification;
DOI:10.1016/S0968-0896(98)80017-5

Reference yield: 56.0%

: 204588-77-2
2,2-dimethyl-3-butynoic acid benzyl ester

: 204588-85-2
1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose

: 204588-86-3
1-[7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose

Guidance literature:: With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80 ℃; for 5h;
DOI:10.1016/S0968-0896(98)80017-5

Reference yield:

: 204588-77-2
2,2-dimethyl-3-butynoic acid benzyl ester

: 204588-85-2
1-[7-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-acetyl-α-L-fucopyranose

: 2,2-Dimethyl-4-[(S)-8-((2R,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-5,6,7,8-tetrahydro-naphthalen-2-yl]-but-3-ynoic acid benzyl ester

: 2,2-Dimethyl-4-[(R)-8-((2R,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-5,6,7,8-tetrahydro-naphthalen-2-yl]-but-3-ynoic acid benzyl ester

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/S0040-4039(98)00468-7