3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 927680-51-1
• Molecular Formula: C₇₀H₈₂N₂O₁₈
• Molecular Weight: 1239.42

Synonyms:3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property of 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

There total 15 articles about 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 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: 63.0%

C65H74N2O16 + 3-Hydroxy-3-methylbutyric acid (625-08-1) → 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside + 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (927680-51-1)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1002/chem.200601245

Reference yield:

ethyl 2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (142776-67-8) → 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (927680-51-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 72 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethaneulfonic acid / CH₂Cl₂ / 0 °C

2: 78 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethaneulfonic acid / CH₂Cl₂ / 0 °C

3: 93 percent / hyrazine acetate / methanol; CH₂Cl₂ / 4 h / 20 °C

4: 76 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethaneulfonic acid / CH₂Cl₂ / 0 °C

5: 93 percent / hyrazine acetate / methanol; CH₂Cl₂ / 4 h / 20 °C

6: 51 percent / silver(I) oxide / dimethyl sulfide / tetrahydrofuran / 20 °C

7: 99 percent / 1,3-propanedithiol; triethylamine; pyridine / H₂O / 20 °C

8: 63 percent / HATU; 1-hydroxy-7-azabenzotriazole; diisopropylethylamine / dimethylformamide / 4 h / 20 °C

With pyridine; 1.3-propanedithiol; N-iodo-succinimide; 1-hydroxy-7-aza-benzotriazole; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrazinium monoacetate; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; silver(l) oxide; dimethylsulfide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.200601245

Reference yield:

4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-methyl-tetrahydro-pyran-3-yl ester (927680-56-6) → 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (927680-51-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 52 percent / tetrabutylammonium bromide / toluene / 3 h / Heating

2.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 0.42 g / sodium azide / dimethylformamide / 40 °C

4.1: 76 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethaneulfonic acid / CH₂Cl₂ / 0 °C

5.1: 93 percent / hyrazine acetate / methanol; CH₂Cl₂ / 4 h / 20 °C

6.1: 51 percent / silver(I) oxide / dimethyl sulfide / tetrahydrofuran / 20 °C

7.1: 99 percent / 1,3-propanedithiol; triethylamine; pyridine / H₂O / 20 °C

8.1: 63 percent / HATU; 1-hydroxy-7-azabenzotriazole; diisopropylethylamine / dimethylformamide / 4 h / 20 °C

With pyridine; 1.3-propanedithiol; N-iodo-succinimide; sodium azide; 1-hydroxy-7-aza-benzotriazole; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrazinium monoacetate; di(n-butyl)tin oxide; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; silver(l) oxide; dimethylsulfide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.200601245

upstream raw materials:

3-Hydroxy-3-methylbutyric acid

4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-methyl-tetrahydro-pyran-3-yl ester

ethyl 3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-fucopyranoside

ethyl 3-O-benzyl-2-O-levulinoyl-1-thio-β-D-fucopyranoside

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