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

Base Information

Chemical Name: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
CAS No.:1271132-15-0
Molecular Formula:C₅₉H₆₃ClN₄O₁₂Si
Molecular Weight:1083.71
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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: 93.0%

: 1271132-13-8
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

: 541-88-8
Chloroacetic anhydride

: 1271132-15-0
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

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1021/jo102363d

Reference yield:

: 853646-67-0
phenyl 2,4-di-O-benzyl-1-thio-β-D-galactopyranosidurono-6,3-lactone

: 1271132-15-0
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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / Molecular sieve

1.2: -60 - -45 °C

1.3: -60 - -45 °C

2.1: acetyl chloride / 50 °C

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

With pyridine; 1,1'-sulfinylbisbenzene; acetyl chloride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;
DOI:10.1021/jo102363d

Reference yield:

: phenyl 3,6-O-di-tert-butylsilyl-1-thio-α-D-galactopyranoside

: 1271132-15-0
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

Guidance literature:: Multi-step reaction with 6 steps

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

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water

4.1: 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / Molecular sieve

4.2: -60 - -45 °C

4.3: -60 - -45 °C

5.1: acetyl chloride / 50 °C

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

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 1,1'-sulfinylbisbenzene; tetrabutyl ammonium fluoride; sodium hydride; acetyl chloride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo102363d