phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside
CAS No.:760966-10-7
Molecular Formula:C₃₉H₆₂N₂O₈Si
Molecular Weight:715.015
Hs Code.:

Synonyms:phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside

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Chemical Property of phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside

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Technology Process of phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside

There total 9 articles about phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 760966-10-7
phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: TFA / CH₂Cl₂ / 6 h

3.1: 7.86 g / pyridine / CH₂Cl₂ / 16 h

4.1: Na; amberlite IR-120 (plus) / methanol / 0.08 h

4.2: 85 percent / pyridine / 3 h / 0 °C

5.1: 72 percent / NAN₃ / dimethylformamide / 16 h / 90 °C

6.1: 88 percent / NaH / dimethylformamide / 3 h / 20 °C

7.1: H₂ / Lindlar catalyst / ethanol; ethyl acetate / 2.5 h / 760.05 Torr

8.1: 31 mg / HOBT; DIPEA; HBTU / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium azide; Amberlite IR-120 (plus); hydrogen; sodium; sodium hydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; Lindlar's catalyst; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.05.080

Reference yield:

: 103082-82-2
phenyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

: 760966-10-7
phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: TFA / CH₂Cl₂ / 6 h

3.1: 7.86 g / pyridine / CH₂Cl₂ / 16 h

4.1: Na; amberlite IR-120 (plus) / methanol / 0.08 h

4.2: 85 percent / pyridine / 3 h / 0 °C

5.1: 72 percent / NAN₃ / dimethylformamide / 16 h / 90 °C

6.1: 88 percent / NaH / dimethylformamide / 3 h / 20 °C

7.1: H₂ / Lindlar catalyst / ethanol; ethyl acetate / 2.5 h / 760.05 Torr

8.1: 31 mg / HOBT; DIPEA; HBTU / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium azide; Amberlite IR-120 (plus); hydrogen; sodium; sodium hydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; Lindlar's catalyst; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.05.080

Reference yield:

: 760966-13-0
phenyl 6-azido-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside

: 760966-10-7
phenyl 6-(N-tert-butoxycarbonylvalinyl)amino-6-deoxy-3-O-benzyl-4-O-methyl-2-O-triisopropylsilyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: H₂ / Lindlar catalyst / ethanol; ethyl acetate / 2.5 h / 760.05 Torr

2: 31 mg / HOBT; DIPEA; HBTU / CH₂Cl₂ / 0.5 h / 20 °C

With hydrogen; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In ethanol; dichloromethane; ethyl acetate;
DOI:10.1016/j.tet.2004.05.080