3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam

Base Information

Chemical Name:3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam
CAS No.:250737-25-8
Molecular Formula:C₅₅H₇₃N₃O₉
Molecular Weight:920.199
Hs Code.:

Synonyms:3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam

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Chemical Property of 3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam

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Technology Process of 3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam

There total 3 articles about 3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam 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: 76.0%

: 250737-20-3
2-amino-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-δ-lactam

: (S)-3-(6-Benzyloxycarbonylamino-hexanoyloxy)-tetradecanoic acid

: 250737-25-8
3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam

Guidance literature:: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2593::aid-ejoc2593>3.0.co;2-c

Reference yield:

: 250737-18-9
3,4,6-tri-O-benzyl-2-[(benzyloxycarbonyl)amino]-2-deoxy-D-glucono-δ-lactam

: 250737-25-8
3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / hydrogen; formic acid / 5 percent Pd/C / H₂O; ethyl acetate; propan-2-ol / 2 h

2: 76 percent / PyBOP; DiPEA / CH₂Cl₂ / 0.5 h

With formic acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; water; ethyl acetate; isopropyl alcohol; 1: Hydrogenation / 2: Acylation;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2593::aid-ejoc2593>3.0.co;2-c

Reference yield:

: 250737-16-7
3,4,6-tri-O-benzyl-2-[(benzyloxycarbonyl)amino]-5-dehydro-2-deoxy-5-hydroxy-D-glucono-δ-lactam

: 250737-25-8
3,4,5-tri-O-benzyl-2-[(R)-3-(6-benzyloxycarbonyl)aminohexanoyloxytetradecanoylamino]-2-deoxy-D-glucono-δ-lactam

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / NaCNBH₃; formic acid / acetonitrile / 2 h / Heating

2: 74 percent / hydrogen; formic acid / 5 percent Pd/C / H₂O; ethyl acetate; propan-2-ol / 2 h

3: 76 percent / PyBOP; DiPEA / CH₂Cl₂ / 0.5 h

With formic acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; water; ethyl acetate; isopropyl alcohol; acetonitrile; 1: Reduction / 2: Hydrogenation / 3: Acylation;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2593::aid-ejoc2593>3.0.co;2-c