2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(1→3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Base Information

Chemical Name:2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(1→3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
CAS No.:1403682-94-9
Molecular Formula:C₄₅H₅₆N₂O₁₅
Molecular Weight:864.944
Hs Code.:

2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(1→3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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Chemical Property of 2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(1→3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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Technology Process of 2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(1→3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

There total 6 articles about 2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(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:

: 625-08-1
3-Hydroxy-3-methylbutyric acid

: 1403682-93-8
C₄₀H₄₈N₂O₁₃

: 1403682-94-9
2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(1→3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: With 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 18h; Inert atmosphere;
DOI:10.1039/c2ob26131f

Reference yield:

: 1314865-02-5
methyl 2-O-acetyl-4-azido-4,6-dideoxy-α-D-glucopyranoside

: 1403682-94-9
2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(1→3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: sulfuric acid; acetic acid / 6 h / 20 °C

2: benzylamine / tetrahydrofuran / 20 °C / Inert atmosphere

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 20 °C

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -40 - -20 °C / Molecular sieve; Inert atmosphere

5: sodium tetrahydroborate; nickel(II) chloride hexahydrate / dichloromethane; ethanol / 1 h / 20 °C

6: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; benzylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c2ob26131f

Reference yield:

: 2,3-di-O-acetyl-4-azido-4,6-dideoxy-D-glucopyranose

: 1403682-94-9
2-[N-(benzyloxycarbonyl)amino]ethyl [2,3-di-O-acetyl-4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl]-(1→3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -40 - -20 °C / Molecular sieve; Inert atmosphere

3: sodium tetrahydroborate; nickel(II) chloride hexahydrate / dichloromethane; ethanol / 1 h / 20 °C

4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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 ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c2ob26131f