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

Base Information

Chemical Name:3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-2-O-(trimethylsilyl)-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester
CAS No.:1407159-26-5
Molecular Formula:C₃₃H₄₆N₄O₁₁Si
Molecular Weight:702.834
Hs Code.:

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

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Chemical Property of 3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-2-O-(trimethylsilyl)-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester

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Technology Process of 3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-2-O-(trimethylsilyl)-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester

There total 2 articles about 3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-2-O-(trimethylsilyl)-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester 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: 75.0%

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

: 1407159-10-7
phenyl 6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-2-O-(trimethylsilyl)-1-thio-α-D-mannopyranoside

: 1407159-26-5
3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-2-O-(trimethylsilyl)-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester

Guidance literature:: phenyl 6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-2-O-(trimethylsilyl)-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; optical yield given as %ee; 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

: 1407159-26-5
3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-2-O-(trimethylsilyl)-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / -60 - 20 °C / Inert atmosphere; Molecular sieve

2.2: 0.33 h / -20 °C / Inert atmosphere; Molecular sieve

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