4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine

Base Information

Chemical Name:4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine
CAS No.:294623-65-7
Molecular Formula:C₄₁H₄₇NO₈
Molecular Weight:681.826
Hs Code.:

Synonyms:4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine

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Chemical Property of 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine

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Technology Process of 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine

There total 9 articles about 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 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: 60.0%

: 127061-08-9
2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride

: 294623-64-6
(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine

: 294623-65-7
4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine

Guidance literature:: With di-tert-butyl peroxide; silver perchlorate; tin(IV) oxide; In diethyl ether; for 48h; Heating;
DOI:10.1080/07328300008544095

Reference yield:

: 33164-03-3
methyl 2,3-di-O-benzyl-α-D-altropyranoside

: 294623-65-7
4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / I₂; PPh₃; imidazole / toluene / 0.25 h / 50 °C

2: 87 percent / pyridine / 16 h / 20 °C

3: 80 percent / NaBH₃CN; Zn / ethanol; H₂O / 16 h / Heating

4: H₂; HCl / Pd/C / methanol

5: 0.9 g / Na₂CO₃ / H₂O / 0.5 h / 0 °C

6: 60 percent / SnO₂; AgClO₄; DTBP / diethyl ether / 48 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; di-tert-butyl peroxide; hydrogen; iodine; silver perchlorate; sodium cyanoborohydride; sodium carbonate; tin(IV) oxide; triphenylphosphine; zinc; palladium on activated charcoal; In methanol; diethyl ether; ethanol; water; toluene; 1: Iodination / 2: Condensation / 3: reductive elimination; reductive amination / 4: Hydrogenolysis / 5: Condensation / 6: Condensation;
DOI:10.1080/07328300008544095

Reference yield:

: 5328-47-2
(4aR,6S,7S,8S,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 294623-65-7
4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / KOH / toluene / 4 h / Heating

2: 98 percent / I₂ / methanol / 2 h / Heating

3: 78 percent / I₂; PPh₃; imidazole / toluene / 0.25 h / 50 °C

4: 87 percent / pyridine / 16 h / 20 °C

5: 80 percent / NaBH₃CN; Zn / ethanol; H₂O / 16 h / Heating

6: H₂; HCl / Pd/C / methanol

7: 0.9 g / Na₂CO₃ / H₂O / 0.5 h / 0 °C

8: 60 percent / SnO₂; AgClO₄; DTBP / diethyl ether / 48 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; di-tert-butyl peroxide; hydrogen; iodine; silver perchlorate; sodium cyanoborohydride; sodium carbonate; tin(IV) oxide; triphenylphosphine; zinc; palladium on activated charcoal; In methanol; diethyl ether; ethanol; water; toluene; 1: Etherification / 2: ether cleavage / 3: Iodination / 4: Condensation / 5: reductive elimination; reductive amination / 6: Hydrogenolysis / 7: Condensation / 8: Condensation;
DOI:10.1080/07328300008544095