2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-D-glucitol

Base Information

Chemical Name:2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-D-glucitol
CAS No.:243131-88-6
Molecular Formula:C₂₁H₃₂N₂O₆
Molecular Weight:408.495
Hs Code.:

Synonyms:2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-D-glucitol

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Chemical Property of 2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-D-glucitol

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Technology Process of 2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-D-glucitol

There total 8 articles about 2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-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:

: (4aS,6R,7R,7aR)-7-Hydroxy-6-{[1-hydroxymethyl-prop-(E)-ylideneamino]-methyl}-2,2-dimethyl-tetrahydro-[1,3]dioxino[5,4-b]pyrrole-5-carboxylic acid benzyl ester

: 243131-88-6
2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-D-glucitol

Guidance literature:: With sodium cyanoborohydride; acetic acid; In methanol; at 25 ℃; for 24h;
DOI:10.1016/S0008-6215(99)00069-5

Reference yield:

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

: 243131-88-6
2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-D-glucitol

Guidance literature:: Multi-step reaction with 7 steps

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

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

3: 57 percent / pyridine / 18 h / -5 °C

4: 76 percent / NaN₃ / dimethylformamide / 24 h / 100 °C

5: H₂ / Raney nickel / ethanol / 4 h / 25 °C

6: methanol

7: HOAc; NaCNBH₃ / methanol / 24 h / 25 °C

With sodium azide; perchloric acid; hydrogen; sodium cyanoborohydride; acetic acid; nickel; In 1,4-dioxane; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; 1: benzyloxycarbonylation / 2: ketalization / 3: Tosylation / 4: Substitution / 5: Hydrogenation / 6: Condensation / 7: Hydrogenation;
DOI:10.1016/S0008-6215(99)00069-5

Reference yield:

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

: 243131-88-6
2,5-anhydro-N-benzyloxycarbonyl-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-1,3-O-isopropylidene-D-glucitol

Guidance literature:: Multi-step reaction with 7 steps

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

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

3: 57 percent / pyridine / 18 h / -5 °C

4: 76 percent / NaN₃ / dimethylformamide / 24 h / 100 °C

5: H₂ / Raney nickel / ethanol / 4 h / 25 °C

6: methanol

7: HOAc; NaCNBH₃ / methanol / 24 h / 25 °C

With sodium azide; perchloric acid; hydrogen; sodium cyanoborohydride; acetic acid; nickel; In 1,4-dioxane; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; 1: benzyloxycarbonylation / 2: ketalization / 3: Tosylation / 4: Substitution / 5: Hydrogenation / 6: Condensation / 7: Hydrogenation;
DOI:10.1016/S0008-6215(99)00069-5