4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine

Base Information

Chemical Name:4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine
CAS No.:294623-69-1
Molecular Formula:C₄₇H₅₇NO₁₃
Molecular Weight:843.968
Hs Code.:

Synonyms:4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine

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Chemical Property of 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine

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Technology Process of 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine

There total 11 articles about 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine 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: 63.0%

: 294623-68-0
4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine

: 294623-69-1
4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine

Guidance literature:: With sodium methylate; In methanol; at 0 ℃; for 4h;
DOI:10.1080/07328300008544095

Reference yield:

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

: 294623-69-1
4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine

Guidance literature:: Multi-step reaction with 8 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

7: 65 percent / AgOTF; sym-collidine; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -78 - -10 °C

8: 63 percent / MeONa / methanol / 4 h / 0 °C

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; hydrogenchloride; di-tert-butyl peroxide; 4 A molecular sieve; hydrogen; iodine; sodium methylate; silver trifluoromethanesulfonate; silver perchlorate; sodium cyanoborohydride; sodium carbonate; tin(IV) oxide; triphenylphosphine; zinc; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; water; toluene; 1: Iodination / 2: Condensation / 3: reductive elimination; reductive amination / 4: Hydrogenolysis / 5: Condensation / 6: Condensation / 7: Condensation / 8: ester cleavage;
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

: 294623-69-1
4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine

Guidance literature:: Multi-step reaction with 10 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

9: 65 percent / AgOTF; sym-collidine; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -78 - -10 °C

10: 63 percent / MeONa / methanol / 4 h / 0 °C

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; hydrogenchloride; potassium hydroxide; di-tert-butyl peroxide; 4 A molecular sieve; hydrogen; iodine; sodium methylate; silver trifluoromethanesulfonate; silver perchlorate; sodium cyanoborohydride; sodium carbonate; tin(IV) oxide; triphenylphosphine; zinc; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; water; toluene; 1: Etherification / 2: ether cleavage / 3: Iodination / 4: Condensation / 5: reductive elimination; reductive amination / 6: Hydrogenolysis / 7: Condensation / 8: Condensation / 9: Condensation / 10: ester cleavage;
DOI:10.1080/07328300008544095