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

Base Information

Chemical Name: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
CAS No.:1407159-09-4
Molecular Formula:C₂₄H₃₉N₃O₆SSi
Molecular Weight:525.742
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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: 93.0%

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

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 12h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201200084

Reference yield: 83.0%

: 21209-51-8
N-benzyloxycarbonyl-L-serine benzyl ester

: 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

: 1407159-25-4
3-O-{6-azido-2-O-(tert-butyldimethylsilyl)-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester

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

N-benzyloxycarbonyl-L-serine benzyl ester; In dichloromethane; at -20 ℃; for 0.333333h; Inert atmosphere; Molecular sieve;
DOI:10.1002/ejoc.201200084

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