O³-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester

Base Information

• Chemical Name: O³-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester
• CAS No.: 174811-18-8
• Molecular Formula: C₅₂H₄₄N₂O₁₄
• Molecular Weight: 920.926

Synonyms:O³-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester

Chemical Property of O³-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester

Chemical Property:

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Technology Process of O³-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester

There total 6 articles about O³-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester 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: 50.0%

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) + 3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-lyxo-hexopyranosyl bromide (174811-12-2) → O3-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester + O3-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester (174811-18-8)

Guidance literature:

With molecular sieve; silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1248/cpb.44.15

Reference yield: 33.0%

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) + 3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-lyxo-hexopyranosyl N,N-diethyldithiocarbonate (174811-13-3) → O3-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester + O3-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester (174811-18-8)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; molecular sieve; methyl trifluoromethanesulfonate; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1248/cpb.44.15

Reference yield:

benzoyl chloride (98-88-4) → O3-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl]-N-benzyloxycarbonyl-L-serine benzyl ester (174811-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / pyridine / 4 h

2: 90 percent / N-bromosuccinimide / CCl₄ / 0.5 h / Heating; Irradiation

3: 50 percent / 1,1,3,3-tetramethylurea, AgOTF, molecular sieves / CH₂Cl₂ / 20 h / Ambient temperature

With pyridine; N-Bromosuccinimide; molecular sieve; silver trifluoromethanesulfonate; tetramethylurea; In tetrachloromethane; dichloromethane;

DOI:10.1248/cpb.44.15

upstream raw materials:

N-benzyloxycarbonyl-L-serine benzyl ester

3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-lyxo-hexopyranosyl N,N-diethyldithiocarbonate

3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-lyxo-hexopyranosyl bromide

benzoyl chloride

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