benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside

Base Information

Chemical Name:benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside
CAS No.:203435-18-1
Molecular Formula:C₆₈H₆₉NO₂₂S
Molecular Weight:1284.36
Hs Code.:

benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside

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Chemical Property of benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside

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Technology Process of benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside

There total 8 articles about benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside 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:

: 150-76-5
4-methoxy-phenol

: 203435-18-1
benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 70 °C

2: 63 percent / molecular sieves 4A, trimethylsilyl triflate / CH₂Cl₂ / Ambient temperature

3: 1.) 2)2>PF₆, hydrogen, 2.) I₂ / 1.) THF, room temperature, 2 h, 2.) THF, water, room temperature, 3 h

4: 1.) pyridine, thionyl chloride, 2.) sodium periodate, RuCl₃*H₂O / 1.) THF, 10 deg C; other reagent: thionyl chloride/triethylamine, 2.) CCl₄, acetonitrile, water, 0 deg C, 1 h

With pyridine; ruthenium trichloride; sodium periodate; thionyl chloride; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; 4 A molecular sieve; hydrogen; iodine; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo971784a

Reference yield:

: 176300-16-6
benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside

: 203435-18-1
benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DMF, 5 min, 2.) DMF, room temperature, 1 h

2: 91 percent / camphorsulfonic acid / methanol / 1 h / 60 °C

3: 90 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 70 °C

4: 63 percent / molecular sieves 4A, trimethylsilyl triflate / CH₂Cl₂ / Ambient temperature

5: 1.) 2)2>PF₆, hydrogen, 2.) I₂ / 1.) THF, room temperature, 2 h, 2.) THF, water, room temperature, 3 h

6: 1.) pyridine, thionyl chloride, 2.) sodium periodate, RuCl₃*H₂O / 1.) THF, 10 deg C; other reagent: thionyl chloride/triethylamine, 2.) CCl₄, acetonitrile, water, 0 deg C, 1 h

With pyridine; ruthenium trichloride; sodium periodate; thionyl chloride; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; iodine; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo971784a

Reference yield:

: 203435-11-4
N-((2R,3R,4S,5S,6R)-4-Allyloxy-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide

: 203435-18-1
benzyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)]-2-acetamido-2-deoxy-6-O-(p-methoxyphenyl)-3-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 70 °C

2: 63 percent / molecular sieves 4A, trimethylsilyl triflate / CH₂Cl₂ / Ambient temperature

3: 1.) 2)2>PF₆, hydrogen, 2.) I₂ / 1.) THF, room temperature, 2 h, 2.) THF, water, room temperature, 3 h

4: 1.) pyridine, thionyl chloride, 2.) sodium periodate, RuCl₃*H₂O / 1.) THF, 10 deg C; other reagent: thionyl chloride/triethylamine, 2.) CCl₄, acetonitrile, water, 0 deg C, 1 h

With pyridine; ruthenium trichloride; sodium periodate; thionyl chloride; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; 4 A molecular sieve; hydrogen; iodine; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo971784a