4-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-glucopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-Ocyclohexylidene-2-deoxystreptamine

Base Information

Chemical Name:4-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-glucopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-Ocyclohexylidene-2-deoxystreptamine
CAS No.:1407159-16-3
Molecular Formula:C₄₀H₅₃N₅O₁₃
Molecular Weight:811.887
Hs Code.:

4-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-glucopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-Ocyclohexylidene-2-deoxystreptamine

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Chemical Property of 4-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-glucopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-Ocyclohexylidene-2-deoxystreptamine

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Technology Process of 4-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-glucopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-Ocyclohexylidene-2-deoxystreptamine

There total 5 articles about 4-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-glucopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-Ocyclohexylidene-2-deoxystreptamine 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:

: 82509-76-0
dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

: 1407159-16-3
4-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-glucopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-Ocyclohexylidene-2-deoxystreptamine

Guidance literature:: Multi-step reaction with 4 steps

1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.33 h / -60 - 20 °C / Inert atmosphere; Molecular sieve

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 10 h / Inert atmosphere

4: L-Selectride / tetrahydrofuran / 10 h / Inert atmosphere

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; L-Selectride; Dess-Martin periodane; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201200084

Reference yield:

: 876862-55-4
phenyl 6-azido-6-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannopyranoside

: 1407159-16-3
4-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-glucopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-Ocyclohexylidene-2-deoxystreptamine

Guidance literature:: Multi-step reaction with 5 steps

1: lithium hexamethyldisilazane / acetonitrile / 24 h / Molecular sieve; Inert atmosphere

2: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.33 h / -60 - 20 °C / Inert atmosphere; Molecular sieve

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / Inert atmosphere

4: Dess-Martin periodane / dichloromethane / 10 h / Inert atmosphere

5: L-Selectride / tetrahydrofuran / 10 h / Inert atmosphere

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; L-Selectride; Dess-Martin periodane; lithium hexamethyldisilazane; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1002/ejoc.201200084