tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate

Base Information

Chemical Name:tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate
CAS No.:134258-58-5
Molecular Formula:C₂₆H₄₂N₄O₈SSi
Molecular Weight:598.793
Hs Code.:

Synonyms:tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate

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Chemical Property of tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate

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Technology Process of tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate

There total 13 articles about tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate 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: 75.0%

: 134258-57-4
tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-D-ido-heptonate

: 134258-58-5
tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 3h; 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

: 134258-58-5
tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate

Guidance literature:: Multi-step reaction with 13 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: 10 percent / N-methyl-morpholine N-oxide, OsO₄ / acetone / 16 h / Ambient temperature

12: 81 percent / pyridine / a.) 0 deg C, 30 min, b.) r. t., 12 h

13: 75 percent / periodinane / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; potassium nitrite; 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:

: 134258-29-0
tert-butyl (benzyl 2-acetamido-2,4-dideoxy-β-L-threo-hex-4-enopyranosid)uronate

: 134258-58-5
tert-butyl 5-acetamido-2-azido-4-O-<(tert-butyl)dimethylsilyl>-2,3,5-trideoxy-7-O-(4-tolylsulfonyl)-L-xylo-6-heptulosonate

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / 2,6-dimethylpyridine / dimethylformamide / 24 h / Ambient temperature

2: 88 percent / H₂ / 10percent Pd-C / methanol / 192 h

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

4: 88 percent / Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

5: 68 percent / KNO₂ / dimethylformamide / 1 h / 100 °C

6: Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

7: 75 percent / dimethylformamide / 12 h / Ambient temperature

8: 10 percent / N-methyl-morpholine N-oxide, OsO₄ / acetone / 16 h / Ambient temperature

9: 81 percent / pyridine / a.) 0 deg C, 30 min, b.) r. t., 12 h

10: 75 percent / periodinane / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; potassium nitrite; hydrogen; 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