methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside
CAS No.:470665-62-4
Molecular Formula:C₄₉H₈₃N₅O₁₀
Molecular Weight:902.226
Hs Code.:

Synonyms:methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside

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Chemical Property of methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside

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Technology Process of methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside

There total 10 articles about methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-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: 73.0%

: 470665-59-9
methyl 2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2-deoxy-3-O-tetradecanoyl-6-O-tosyl-α-D-glucopyranoside

: 470665-62-4
methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃;
DOI:10.1081/CAR-120004331

Reference yield:

: 14131-62-5
D-glucosamine hydrochloride

: 470665-62-4
methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 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 / PyBOP; (i-Pr)2NEt / CH₂Cl₂

7: 87 percent / TFA / tetrahydrofuran; H₂O / 0 - 20 °C

8: 79 percent / pyridine / 96 h

9: 73 percent / NaN₃ / dimethylformamide / 80 °C

With hydrogenchloride; dmap; sodium azide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 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

: 470665-62-4
methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 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 / PyBOP; (i-Pr)2NEt / CH₂Cl₂

6: 87 percent / TFA / tetrahydrofuran; H₂O / 0 - 20 °C

7: 79 percent / pyridine / 96 h

8: 73 percent / NaN₃ / dimethylformamide / 80 °C

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