tert-butyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-D-xylo-hexopyranuronate

Base Information

Chemical Name:tert-butyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-D-xylo-hexopyranuronate
CAS No.:134258-30-3
Molecular Formula:C₁₈H₃₅NO₆Si
Molecular Weight:389.565
Hs Code.:

Synonyms:

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Chemical Property of tert-butyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-D-xylo-hexopyranuronate

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Technology Process of tert-butyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-D-xylo-hexopyranuronate

There total 1 articles about tert-butyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-D-xylo-hexopyranuronate 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: 88.0%

: 134271-33-3
tert-butyl -2,4-dideoxy-β-L-threo-hex-4-enopyranosid>uronate

: 134258-31-4
tert-butyl <(cyclohexyl)methyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-α-D-xylo-hexopyranosid>uronate

: 134258-30-3,134285-85-1
tert-butyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-D-xylo-hexopyranuronate

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 192h;
DOI:10.1002/hlca.19910740214

Reference yield:

: 134258-30-3,134285-85-1
tert-butyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-D-xylo-hexopyranuronate

: 134258-25-6
(2S,4S,5S,6R)-5-acetamido-4-hydroxy-6-(hydroxymethyl)1-phenylpiperidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 11 steps

1: 85 percent / tetrahydrofuran / a.) 1h, 0 deg C b.) 3h, r. t.

2: 88 percent / Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

3: 68 percent / KNO₂ / dimethylformamide / 1 h / 100 °C

4: Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

5: 75 percent / dimethylformamide / 12 h / Ambient temperature

6: 69 percent / N-methyl-morpholine N-oxide, OsO₄ / acetone / 16 h / Ambient temperature

7: 96 percent / 2,6-dimethylpyridine / dimethylformamide / 3 h / Ambient temperature

8: 94 percent / periodinane / CH₂Cl₂ / 4 h / Ambient temperature

9: 79 percent / H₂ / 10percent Pd-C / methanol / 4 h / 760 Torr

10: 39 percent / Cu(OAc)2 / CH₂Cl₂ / 72 h / Ambient temperature

11: 80 percent / CF₃COOH/H₂O (4:1) / CH₂Cl₂ / 12 h / Ambient temperature

With 2,6-dimethylpyridine; osmium(VIII) oxide; potassium nitrite; copper diacetate; water; hydrogen; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1002/hlca.19910740214

Reference yield:

: 134258-30-3,134285-85-1
tert-butyl 2-acetamido-3-O-<(tert-butyl)dimethylsilyl>-2,4-dideoxy-D-xylo-hexopyranuronate

: 134258-52-9
tert-butyl 5-acetamido-2-N,6:4,7-dianhydro-2-<<(benzyloxy)carbonyl>amino>-2,3,5-L-manno-heptonate

Guidance literature:: Multi-step reaction with 11 steps

1: 85 percent / tetrahydrofuran / a.) 1h, 0 deg C b.) 3h, r. t.

2: 88 percent / Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

3: 68 percent / KNO₂ / dimethylformamide / 1 h / 100 °C

4: Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

5: 75 percent / dimethylformamide / 12 h / Ambient temperature

6: 69 percent / N-methyl-morpholine N-oxide, OsO₄ / acetone / 16 h / Ambient temperature

7: 96 percent / 2,6-dimethylpyridine / dimethylformamide / 3 h / Ambient temperature

8: 94 percent / periodinane / CH₂Cl₂ / 4 h / Ambient temperature

9: 79 percent / H₂ / 10percent Pd-C / methanol / 4 h / 760 Torr

10: aq. NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

11: (diethylamino)sulfur trifluoride (DAST) / CH₂Cl₂ / 216 h / Ambient temperature

With 2,6-dimethylpyridine; osmium(VIII) oxide; potassium nitrite; diethylamino-sulfur trifluoride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1002/hlca.19910740214