2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol

Base Information

Chemical Name:2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol
CAS No.:243131-97-7
Molecular Formula:C₅₀H₆₄N₂O₆Si₂
Molecular Weight:845.239
Hs Code.:

Synonyms:2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol

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Chemical Property of 2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol

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Technology Process of 2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol

There total 10 articles about 2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol 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:

: (2R,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-{[1-hydroxymethyl-prop-(Z)-ylideneamino]-methyl}-pyrrolidine-1-carboxylic acid benzyl ester

: 243131-97-7
2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol

Guidance literature:: With sodium cyanoborohydride; acetic acid; In methanol; at 25 ℃;
DOI:10.1016/S0008-6215(99)00069-5

Reference yield:

: 132295-44-4
2,5-anhydro-2,5-imino-D-glucitol

: 243131-97-7
2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol

Guidance literature:: Multi-step reaction with 9 steps

1: 89 percent / NHCO₃ / dioxane; H₂O / 18 h / 25 °C

2: 96 percent Turnov_. / HClO₄ / acetone / 0.5 h

3: 56 percent / imidazole / dimethylformamide / 24 h / 20 °C

4: 82 percent Turnov_. / AcOH / H₂O; methanol / 24 h / 50 °C

5: 80 percent / I₂; PPh₃; imidazole / toluene / 2.5 h / 108 °C

6: 79 percent / NaN₃ / dimethylformamide / 24 h / 100 °C

7: 82 percent Turnov_. / H₂ / Raney nickel / ethanol / 1 h / 25 °C

8: methanol

9: HOAc; NaCNBH₃ / methanol / 25 °C

With 1H-imidazole; sodium azide; perchloric acid; hydrogen; iodine; sodium cyanoborohydride; acetic acid; triphenylphosphine; nickel; In 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; 1: benzyloxycarbonylation / 2: ketalization / 3: silylation / 4: deprotection / 5: Iodination / 6: Substitution / 7: Hydrogenation / 8: Condensation / 9: Hydrogenation;
DOI:10.1016/S0008-6215(99)00069-5

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 243131-97-7
2,5-anhydro-N-benzyloxycarbonyl-4,6-di-O-tert-butyldiphenylsilyl-1-deoxy-1-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol

Guidance literature:: Multi-step reaction with 9 steps

1: 89 percent / NHCO₃ / dioxane; H₂O / 18 h / 25 °C

2: 96 percent Turnov_. / HClO₄ / acetone / 0.5 h

3: 56 percent / imidazole / dimethylformamide / 24 h / 20 °C

4: 82 percent Turnov_. / AcOH / H₂O; methanol / 24 h / 50 °C

5: 80 percent / I₂; PPh₃; imidazole / toluene / 2.5 h / 108 °C

6: 79 percent / NaN₃ / dimethylformamide / 24 h / 100 °C

7: 82 percent Turnov_. / H₂ / Raney nickel / ethanol / 1 h / 25 °C

8: methanol

9: HOAc; NaCNBH₃ / methanol / 25 °C

With 1H-imidazole; sodium azide; perchloric acid; hydrogen; iodine; sodium cyanoborohydride; acetic acid; triphenylphosphine; nickel; In 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; 1: benzyloxycarbonylation / 2: ketalization / 3: silylation / 4: deprotection / 5: Iodination / 6: Substitution / 7: Hydrogenation / 8: Condensation / 9: Hydrogenation;
DOI:10.1016/S0008-6215(99)00069-5