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

Base Information

Chemical Name:1-[7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose
CAS No.:204588-80-7
Molecular Formula:C₅₀H₅₂O₇
Molecular Weight:764.959
Hs Code.:

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

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Chemical Property of 1-[7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose

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Technology Process of 1-[7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose

There total 6 articles about 1-[7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-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: 26.0%

: 33639-77-9
perbenzyl fucosyl bromide

: 204588-79-4
7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthol

: 204588-80-7
1-[7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose

Guidance literature:: With 4 A molecular sieve; tetraethylammonium bromide; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/S0968-0896(98)80017-5

Reference yield:

: 56663-76-4
2,2-dimethyl-3-butynoic acid

: 204588-80-7
1-[7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / DCC; DMAP / CH₂Cl₂

2: 57 percent / triethylamine / PdCl₂(PPh₃)2 / dimethylformamide / 70 °C

3: 72 percent / sodium borohydride / methanol / 1 h

4: 26 percent / tetraethylammonium bromide; 4 Angstroem molecular sieves / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium tetrahydroborate; 4 A molecular sieve; tetraethylammonium bromide; triethylamine; dicyclohexyl-carbodiimide; bis-triphenylphosphine-palladium(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Condensation / 3: Reduction / 4: Condensation;
DOI:10.1016/S0968-0896(98)80017-5

Reference yield:

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

: 204588-80-7
1-[7-[3-(benzyloxycarbonyl)-3,3-dimethyl-1-propynyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose

Guidance literature:: Multi-step reaction with 3 steps

1: 57 percent / triethylamine / PdCl₂(PPh₃)2 / dimethylformamide / 70 °C

2: 72 percent / sodium borohydride / methanol / 1 h

3: 26 percent / tetraethylammonium bromide; 4 Angstroem molecular sieves / CH₂Cl₂ / 24 h / 20 °C

With sodium tetrahydroborate; 4 A molecular sieve; tetraethylammonium bromide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Reduction / 3: Condensation;
DOI:10.1016/S0968-0896(98)80017-5