3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam

Base Information

Chemical Name:3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam
CAS No.:259792-27-3
Molecular Formula:C₂₅H₃₂N₄O₄Si
Molecular Weight:480.639
Hs Code.:

Synonyms:3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam

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Chemical Property of 3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam

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Technology Process of 3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam

There total 6 articles about 3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam 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: 80.0%

: 259792-26-2
2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-3-{[bis(4-methoxyphenyl)methyl]amino}-D-mannono-1,3-lactam

: 259792-27-3
3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at -15 - 0 ℃; for 8.5h;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2380::AID-HLCA2380>3.0.CO;2-P

Reference yield:

: 105368-84-1
4-O-[(tert-butyl)diphenylsilyl]-2,3-O-isopropylidene-D-erythrose

: 259792-27-3
3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam

Guidance literature:: Multi-step reaction with 4 steps

1: molecular sieves (3A) / CH₂Cl₂ / 21 h / 0 °C

2: 740 mg / dimethylformamide / 13 h / 25 °C

3: 89 percent / Bu₄NN₃; 1,3-dimethylimidazolidin-2-one / 96 h / 25 - 60 °C

4: 80 percent / ceric ammonium nitrate / acetonitrile; H₂O / 8.5 h / -15 - 0 °C

With 1,3-dimethyl-2-imidazolidinone; ammonium cerium(IV) nitrate; 3 A molecular sieve; tetrabutylammoniun azide; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: cyclocondensation / 3: Substitution / 4: N-dearylation;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2380::AID-HLCA2380>3.0.CO;2-P

Reference yield:

: 259792-14-8
4-O-[(tert-butyl)diphenylsilyl]-D-erythrose dibenzyl dithioacetal

: 259792-27-3
3-amino-2-azido-6-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-4,5-O-isopropylidene-D-mannono-1,3-lactam

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / CuSO₄ / 168 h / 50 - 55 °C

2: 98 percent / H₂O; CaCO₃; HgCl₂ / acetonitrile / 22 h / 22 °C

3: molecular sieves (3A) / CH₂Cl₂ / 21 h / 0 °C

4: 740 mg / dimethylformamide / 13 h / 25 °C

5: 89 percent / Bu₄NN₃; 1,3-dimethylimidazolidin-2-one / 96 h / 25 - 60 °C

6: 80 percent / ceric ammonium nitrate / acetonitrile; H₂O / 8.5 h / -15 - 0 °C

With 1,3-dimethyl-2-imidazolidinone; ammonium cerium(IV) nitrate; 3 A molecular sieve; water; tetrabutylammoniun azide; copper(II) sulfate; calcium carbonate; mercury dichloride; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: cyclocondensation / 2: Hydrolysis / 3: Condensation / 4: cyclocondensation / 5: Substitution / 6: N-dearylation;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2380::AID-HLCA2380>3.0.CO;2-P