methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside

Base Information

• Chemical Name: methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside
• CAS No.: 174089-91-9
• Molecular Formula: C₂₆H₃₄O₁₃
• Molecular Weight: 554.548

Synonyms:methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside

Chemical Property of methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside

Chemical Property:

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Technology Process of methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside

There total 5 articles about methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside 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:

Benzoic acid (2S,3S,4R,5S,6R)-6-benzyloxymethyl-4-((2R,3S,5S,6R)-3,5-diacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5-iodo-2-methoxy-tetrahydro-pyran-3-yl ester → methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside (174089-91-9)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In ethyl acetate; under 3000.2 Torr; Yield given;

DOI:10.1016/0008-6215(95)00268-5

Reference yield:

methyl 2-O-benzoyl-4, 6-O-benzylidene-α-D-mannopyranoside (91685-06-2) → methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside (174089-91-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / silver trifluoromethanesulfonate, 2,6-di-tert-butyl-4-methylpyridine, 4 Angstroem molecular sieves / toluene; CH₂Cl₂ / 1 h / 0 °C

2: sodium cyanoborohydride / tetrahydrofuran / 0.33 h

3: triiodoimidazole, triphenylphosphine / toluene / 110 °C

4: H₂, aq. NaHCO₃ / Pd-C / ethyl acetate / 3000.2 Torr

With 2,6-di-tert-butyl-4-methylpyridine; tri-iodoimidazole; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; sodium cyanoborohydride; sodium hydrogencarbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1016/0008-6215(95)00268-5

Reference yield:

2,4,6-Tri-O-acetyl-3-deoxy-α-D-arabino-hexapyranosyl chloride (139562-16-6) → methyl 2-O-benzoyl-4-deoxy-3-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside (174089-91-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / silver trifluoromethanesulfonate, 2,6-di-tert-butyl-4-methylpyridine, 4 Angstroem molecular sieves / toluene; CH₂Cl₂ / 1 h / 0 °C

2: sodium cyanoborohydride / tetrahydrofuran / 0.33 h

3: triiodoimidazole, triphenylphosphine / toluene / 110 °C

4: H₂, aq. NaHCO₃ / Pd-C / ethyl acetate / 3000.2 Torr

With 2,6-di-tert-butyl-4-methylpyridine; tri-iodoimidazole; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; sodium cyanoborohydride; sodium hydrogencarbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1016/0008-6215(95)00268-5

upstream raw materials:

methyl 2-O-benzoyl-4, 6-O-benzylidene-α-D-mannopyranoside

2,4,6-Tri-O-acetyl-3-deoxy-α-D-arabino-hexapyranosyl chloride

methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside

Downstream raw materials:

methyl 2-O-benzoyl-4-deoxy-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3-O-(2,4,6-tri-O-acetyl-3-deoxy-α-D-arabino-hexopyranosyl)-α-D-lyxo-hexopyranoside

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