Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester
CAS No.:470665-66-8
Molecular Formula:C₇₈H₁₁₇N₅O₁₃
Molecular Weight:1332.81
Hs Code.:

Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

Synonyms:Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

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Chemical Property of Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

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Technology Process of Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

There total 16 articles about Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl 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: 96.0%

: 470665-46-4
3,4,6-tri-O-benzyl-1,5-N-[carboxymethylimino]-2-(tetradecanoyl)amino-1,2,5-trideoxy-D-glucitol

: 470665-63-5
methyl 6-amino-2-[(6-benzyloxycarbonylamino)hexanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside

: 470665-66-8
Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

Guidance literature:: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1h;
DOI:10.1081/CAR-120004331

Reference yield:

: 14131-62-5
D-glucosamine hydrochloride

: 470665-66-8
Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: NaHCO₃ / H₂O / 16 h / 20 °C

2: 16 g / HCl / 7 h / Heating

3: 100 percent / p-toluenesulfonic acid / acetone; CH₂Cl₂ / 16 h / 20 °C

4: 86 percent / DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

5: 100 percent / H₂ / Pd/C / ethyl acetate / 66 h / 760 Torr

6: 87 percent / (i-Pr)2NEt; PyBOP / CH₂Cl₂ / 1 h

7: 99 percent / TFA / tetrahydrofuran; H₂O / 0 - 20 °C

8: 80 percent / pyridine / 24 h

9: 84 percent / NaN₃ / dimethylformamide / 4 h / 70 °C

10: 100 percent / PPh₃; H₂O / tetrahydrofuran / 3.5 h / Heating

11: 96 percent / PyBOP; (i-Pr)2NEt / CH₂Cl₂ / 1 h

With hydrogenchloride; dmap; sodium azide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1081/CAR-120004331

Reference yield:

: 77059-32-6
benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

: 470665-66-8
Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 16 g / HCl / 7 h / Heating

2: 100 percent / p-toluenesulfonic acid / acetone; CH₂Cl₂ / 16 h / 20 °C

3: 86 percent / DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

4: 100 percent / H₂ / Pd/C / ethyl acetate / 66 h / 760 Torr

5: 87 percent / (i-Pr)2NEt; PyBOP / CH₂Cl₂ / 1 h

6: 99 percent / TFA / tetrahydrofuran; H₂O / 0 - 20 °C

7: 80 percent / pyridine / 24 h

8: 84 percent / NaN₃ / dimethylformamide / 4 h / 70 °C

9: 100 percent / PPh₃; H₂O / tetrahydrofuran / 3.5 h / Heating

10: 96 percent / PyBOP; (i-Pr)2NEt / CH₂Cl₂ / 1 h

With hydrogenchloride; dmap; sodium azide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1081/CAR-120004331