benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranose

Base Information

• Chemical Name: benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranose
• CAS No.: 1271132-17-2
• Molecular Formula: C₄₃H₄₅ClN₄O₁₂
• Molecular Weight: 845.303

Synonyms:

Chemical Property of benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranose

There total 7 articles about benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranose 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:

benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranoside (1271132-15-0) → benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranose (1271132-17-2) + benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranose

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 70 ℃; optical yield given as %de;

DOI:10.1021/jo102363d

Reference yield:

phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside → benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranose (1271132-17-2) + benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranose

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water

2.1: 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / Molecular sieve

2.2: -60 - -45 °C

2.3: -60 - -45 °C

3.1: acetyl chloride / 50 °C

4.1: pyridine / dichloromethane / 2.5 h / 20 °C

5.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 70 °C

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 1,1'-sulfinylbisbenzene; triethylamine tris(hydrogen fluoride); acetyl chloride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo102363d

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranose (1271132-17-2) + benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranose

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water

5.1: 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / Molecular sieve

5.2: -60 - -45 °C

5.3: -60 - -45 °C

6.1: acetyl chloride / 50 °C

7.1: pyridine / dichloromethane / 2.5 h / 20 °C

8.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 70 °C

With pyridine; 1H-imidazole; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 1,1'-sulfinylbisbenzene; tetrabutyl ammonium fluoride; sodium hydride; triethylamine tris(hydrogen fluoride); acetyl chloride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jo102363d

upstream raw materials:

2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranoside

benzyl 2,4-di-O-benzyl-α-D-galactopyranosyluronate-(1->3)-tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranoside

benzyl 2,4-di-O-benzyl-3-O-chloroacetyl-α-D-galactopyranosyluronate-(1->3)-tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranoside

1-thiophenyl-β-D-galactopyranoside

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