tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate

Base Information

Chemical Name:tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate
CAS No.:134258-50-7
Molecular Formula:C₃₁H₅₆N₂O₅Si₂
Molecular Weight:592.967
Hs Code.:

tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate

Synonyms:tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate

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Chemical Property of tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate

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Technology Process of tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate

There total 15 articles about tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate 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: 39.0%

: 28899-97-0,7239-60-3
triphenylbismuth(V) diacetate

: 134258-49-4
tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>-methyl>piperidine-2-carboxylate

: 134258-50-7
tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate

Guidance literature:: With copper diacetate; In dichloromethane; for 72h; Ambient temperature;
DOI:10.1002/hlca.19910740214

Reference yield:

: 33401-01-3,55652-76-1
benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-glucopyranoside

: 134258-50-7
tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate

Guidance literature:: Multi-step reaction with 15 steps

2: 93 percent / 7-methyl-1,5,7-triazabicyclo<4.4.0>dec-5-ene, molecular sieves (4 angstroem) / toluene / 3 h / Heating

3: 98 percent / 2.5 M NaOMe / methanol / 20 h

4: 93 percent / 2,6-dimethylpyridine / dimethylformamide / 24 h / Ambient temperature

5: 88 percent / H₂ / 10percent Pd-C / methanol / 192 h

6: 85 percent / tetrahydrofuran / a.) 1h, 0 deg C b.) 3h, r. t.

7: 88 percent / Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

8: 68 percent / KNO₂ / dimethylformamide / 1 h / 100 °C

9: Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

10: 75 percent / dimethylformamide / 12 h / Ambient temperature

11: 69 percent / N-methyl-morpholine N-oxide, OsO₄ / acetone / 16 h / Ambient temperature

12: 96 percent / 2,6-dimethylpyridine / dimethylformamide / 3 h / Ambient temperature

13: 94 percent / periodinane / CH₂Cl₂ / 4 h / Ambient temperature

14: 79 percent / H₂ / 10percent Pd-C / methanol / 4 h / 760 Torr

15: 39 percent / Cu(OAc)2 / CH₂Cl₂ / 72 h / Ambient temperature

With 2,6-dimethylpyridine; osmium(VIII) oxide; potassium nitrite; copper diacetate; 4 A molecular sieve; hydrogen; sodium methylate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/hlca.19910740214

Reference yield:

: 134258-34-7
tert-butyl 5-acetamido-4-O-<(tert-butyl)dimethylsilyl>-3,5,6,7-tetradeoxy-L-lyxo-hept-6-enonate

: 134258-50-7
tert-butyl (2S,4S,5S,6R)-5-acetamido-4-<(tert-butyl)dimethylsilyloxy>-6-<<(tert-butyl)dimethylsilyloxy>methyl>-1-phenylpiperidine-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

2: 75 percent / dimethylformamide / 12 h / Ambient temperature

3: 69 percent / N-methyl-morpholine N-oxide, OsO₄ / acetone / 16 h / Ambient temperature

4: 96 percent / 2,6-dimethylpyridine / dimethylformamide / 3 h / Ambient temperature

5: 94 percent / periodinane / CH₂Cl₂ / 4 h / Ambient temperature

6: 79 percent / H₂ / 10percent Pd-C / methanol / 4 h / 760 Torr

7: 39 percent / Cu(OAc)2 / CH₂Cl₂ / 72 h / Ambient temperature

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