2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone

Base Information

Chemical Name:2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone
CAS No.:83093-86-1
Molecular Formula:C₃₆H₃₇NO₈
Molecular Weight:611.692
Hs Code.:

Synonyms:2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone

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Chemical Property of 2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone

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Technology Process of 2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone

There total 10 articles about 2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone 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: 61.0%

: 2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptopyranose

: 83093-86-1
2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone

Guidance literature:: With bromine; barium carbonate; In 1,4-dioxane; water; Ambient temperature;
DOI:10.1016/S0008-6215(00)82223-5

Reference yield:

: 7177-79-9,13035-24-0,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9,13225-19-9
methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

: 83093-86-1
2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone

Guidance literature:: Multi-step reaction with 9 steps

1: lithium aluminium hydride-aluminium chloride

2: 92 percent / dimethyl sulfoxide, phosphoric acid, dicyclohexylcarbodiimide / benzene; pyridine / 7 h / Ambient temperature

3: 63 percent / pyridine / 3 h / Ambient temperature

4: lithium aluminium hydride / diethyl ether / 1 h / Ambient temperature

5: triethylamine / benzene / 2 h / 0 °C

6: 98 percent / 1.5 h / 40 °C

7: 92 percent / cc. sulfuric acid / CHCl₃ / 2 h / Ambient temperature

8: 96 percent / 0.22 M sodium methoxide / methanol / 1 h / Ambient temperature

9: 61 percent / barium carbonate, bromine / dioxane; H₂O / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; phosphoric acid; sulfuric acid; bromine; sodium methylate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; barium carbonate; In 1,4-dioxane; pyridine; methanol; diethyl ether; chloroform; water; benzene;
DOI:10.1016/S0008-6215(00)82223-5

Reference yield:

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 83093-86-1
2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / dimethyl sulfoxide, phosphoric acid, dicyclohexylcarbodiimide / benzene; pyridine / 7 h / Ambient temperature

2: 63 percent / pyridine / 3 h / Ambient temperature

3: lithium aluminium hydride / diethyl ether / 1 h / Ambient temperature

4: triethylamine / benzene / 2 h / 0 °C

5: 98 percent / 1.5 h / 40 °C

6: 92 percent / cc. sulfuric acid / CHCl₃ / 2 h / Ambient temperature

7: 96 percent / 0.22 M sodium methoxide / methanol / 1 h / Ambient temperature

8: 61 percent / barium carbonate, bromine / dioxane; H₂O / Ambient temperature

With lithium aluminium tetrahydride; phosphoric acid; sulfuric acid; bromine; sodium methylate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; barium carbonate; In 1,4-dioxane; pyridine; methanol; diethyl ether; chloroform; water; benzene;
DOI:10.1016/S0008-6215(00)82223-5