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

Base Information

Chemical Name: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
CAS No.:1271132-11-6
Molecular Formula:C₅₀H₅₄N₄O₁₀Si
Molecular Weight:899.085
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 4 articles about 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 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: 75.0%

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

: 1271131-90-8
tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranoside

: 1271132-11-6
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

Guidance literature:: phenyl 2,4-di-O-benzyl-1-thio-β-D-galactopyranosidurono-6,3-lactone; With 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; for 0.5h; Molecular sieve;

With trifluoromethylsulfonic anhydride; In dichloromethane; at -60 - -45 ℃;

tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranoside; With 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 - -45 ℃; diastereoselective reaction;
DOI:10.1021/jo102363d

Reference yield:

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

: 1271132-11-6
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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: phenyl 2,4-di-O-benzyl-1-thio-β-D-galactopyranoside

: 1271132-11-6
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

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water

3.1: 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / Molecular sieve

3.2: -60 - -45 °C

3.3: -60 - -45 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 1,1'-sulfinylbisbenzene; tetrabutyl ammonium fluoride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo102363d