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

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Chemical Name:3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester
CAS No.:1407159-30-1
Molecular Formula:C₃₀H₃₈N₄O₁₁
Molecular Weight:630.652
Hs Code.:

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

There total 3 articles about 3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-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: 96.0%

: 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

: 1407159-30-1
3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 5.5h;
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

: 1407159-30-1
3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 3 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

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 5.5 h

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

Reference yield:

: 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

: 1407159-30-1
3-O-{6-azido-6-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-mannopyranosyl}-N-(benzyloxycarbonyl)-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / -60 - 20 °C / Inert atmosphere; Molecular sieve

1.2: 0.33 h / -20 °C / Inert atmosphere; Molecular sieve

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 5.5 h

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