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

Base Information

Chemical Name:4-O-{6-azido-2-O-(tert-butyldimethylsilyl)-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-O-cyclohexylidene-2-deoxystreptamine
CAS No.:1407159-11-8
Molecular Formula:C₄₆H₆₇N₅O₁₃Si
Molecular Weight:926.149
Hs Code.:

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

Synonyms:4-O-{6-azido-2-O-(tert-butyldimethylsilyl)-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-O-cyclohexylidene-2-deoxystreptamine

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

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

There total 3 articles about 4-O-{6-azido-2-O-(tert-butyldimethylsilyl)-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-O-cyclohexylidene-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: 80.0%

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

: 1407159-09-4
phenyl 6-azido-2-O-(tert-butyldimethylsilyl)-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-1-thio-α-D-mannopyranoside

: 1407159-11-8
4-O-{6-azido-2-O-(tert-butyldimethylsilyl)-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-O-cyclohexylidene-2-deoxystreptamine

Guidance literature:: With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 - 20 ℃; for 0.333333h; stereoselective reaction; Inert atmosphere; Molecular sieve;
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

: 1407159-11-8
4-O-{6-azido-2-O-(tert-butyldimethylsilyl)-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-O-cyclohexylidene-2-deoxystreptamine

Guidance literature:: Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine / dichloromethane / 12 h / 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

With 2,6-dimethylpyridine; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;
DOI:10.1002/ejoc.201200084

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 1407159-11-8
4-O-{6-azido-2-O-(tert-butyldimethylsilyl)-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-1,3-bis[N-(benzyloxycarbonyl)]-5,6-O-cyclohexylidene-2-deoxystreptamine

Guidance literature:: Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine / dichloromethane / 12 h / 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

With 2,6-dimethylpyridine; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;
DOI:10.1002/ejoc.201200084