2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol

Base Information

Chemical Name:2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol
CAS No.:1271132-47-8
Molecular Formula:C₅₁H₅₄N₄O₁₂
Molecular Weight:915.009
Hs Code.:

2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol

Synonyms:2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol

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Chemical Property of 2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol

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Technology Process of 2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol

There total 6 articles about 2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol 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: 70.0%

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

: 1271132-09-2
4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-O-benzyl-sn-glycerol

: 1271132-47-8
2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol

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 ℃;

4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-O-benzyl-sn-glycerol; 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

: 1271132-47-8
2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol

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

: 1271132-47-8
2,4-di-O-benzyl-α-D-galactopyranosiduronyl-3,6-lactone-(1->3)-4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-α-D-galactopyranosyl-(1->3)-1,2-di-O-benzyl-sn-glycerol

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