2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Base Information

Chemical Name:2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol
CAS No.:121624-28-0
Molecular Formula:C₂₄H₂₈N₄O₅
Molecular Weight:452.51
Hs Code.:

Synonyms:2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

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Chemical Property of 2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

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Technology Process of 2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

There total 5 articles about 2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 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: 81.0%

: 100-39-0
benzyl bromide

: 121624-26-8
2-azido-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

: 121624-28-0
2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: With potassium hydroxide; In tetrahydrofuran; at 60 ℃; for 8h;
DOI:10.1016/0008-6215(90)80030-7

Reference yield:

: 114129-23-6
N-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-mannitol

: 121624-28-0
2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / H₂, glacial acetic acid / 10percent Pd-C / methanol / 5 h / 40 °C / 2250.2 Torr

2: 87 percent / K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

3: 99 percent / SOCl₂, NEt₃ / ethyl acetate / 1 h / 0 °C

4: 52 percent / LiN₃ / dimethylformamide / 8 h / 90 °C

5: 81 percent / KOH / tetrahydrofuran / 8 h / 60 °C

With potassium hydroxide; thionyl chloride; lithium azide; hydrogen; potassium carbonate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(90)80030-7

Reference yield:

: 121624-25-7
(3aR,5aR,9aR,9bS)-8,8-Dimethyl-2-oxo-hexahydro-1,3,7,9-tetraoxa-2λ⁴-thia-5-aza-cyclopenta[a]naphthalene-5-carboxylic acid benzyl ester

: 121624-28-0
2-Azido-3-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: Multi-step reaction with 2 steps

1: 52 percent / LiN₃ / dimethylformamide / 8 h / 90 °C

2: 81 percent / KOH / tetrahydrofuran / 8 h / 60 °C

With potassium hydroxide; lithium azide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(90)80030-7