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

Base Information

• Chemical Name: methyl 2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2-deoxy-3-O-tetradecanoyl-6-O-tosyl-α-D-glucopyranoside
• CAS No.: 470665-59-9
• Molecular Formula: C₅₆H₉₀N₂O₁₃S
• Molecular Weight: 1031.4

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

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

There total 8 articles about methyl 2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2-deoxy-3-O-tetradecanoyl-6-O-tosyl-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:

D-glucosamine hydrochloride (14131-62-5) → methyl 2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2-deoxy-3-O-tetradecanoyl-6-O-tosyl-α-D-glucopyranoside (470665-59-9)

Guidance literature:

Multi-step reaction with 8 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

With hydrogenchloride; dmap; 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; acetone;

DOI:10.1081/CAR-120004331

Reference yield:

benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate (77059-32-6) → methyl 2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2-deoxy-3-O-tetradecanoyl-6-O-tosyl-α-D-glucopyranoside (470665-59-9)

Guidance literature:

Multi-step reaction with 7 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

With hydrogenchloride; dmap; 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; acetone;

DOI:10.1081/CAR-120004331

Reference yield:

methyl 2-[(benzyloxycarbonyl)amino]-2-deoxy-4,6-isopropylidene-α-D-glucopyranoside (61348-62-7) → methyl 2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2-deoxy-3-O-tetradecanoyl-6-O-tosyl-α-D-glucopyranoside (470665-59-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

2: 100 percent / H₂ / Pd/C / ethyl acetate / 66 h / 760 Torr

3: 87 percent / PyBOP; (i-Pr)2NEt / CH₂Cl₂

4: 87 percent / TFA / tetrahydrofuran; H₂O / 0 - 20 °C

5: 79 percent / pyridine / 96 h

With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; water; ethyl acetate;

DOI:10.1081/CAR-120004331

upstream raw materials:

D-glucosamine hydrochloride

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

methyl 2-[(benzyloxycarbonyl)amino]-2-deoxy-4,6-isopropylidene-α-D-glucopyranoside

methyl 2-amino-2-deoxy-4,6-isopropylidene-3-O-tetradecanoyl-α-D-glucopyranoside

Downstream raw materials:

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

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

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