5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone

Base Information

Chemical Name:5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone
CAS No.:122767-57-1
Molecular Formula:C₂₂H₃₁NO₇
Molecular Weight:421.491
Hs Code.:

Synonyms:5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone

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Chemical Property of 5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone

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Technology Process of 5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone

There total 13 articles about 5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone 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: 100.0%

: 5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-pentose

: 122767-57-1
5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone

Guidance literature:: With N-iodo-succinimide; tetra-(n-butyl)ammonium iodide; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1016/S0040-4020(01)85597-6

Reference yield: 31.0%

: 5-O-Benzyl-3-tert-butoxycarbonylamino-2,3-dideoxy-5-hydroxymethyl-D-ribo-pentose

: 75-65-0
tert-butyl alcohol

: 122767-57-1
5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone

Guidance literature:: With pyridine; chromium(VI) oxide; acetic anhydride; In dichloromethane; N,N-dimethyl-formamide; for 20h; Ambient temperature;
DOI:10.1016/S0040-4039(00)82339-4

Reference yield:

: 122799-50-2
2-tert-Butoxycarbonylamino-3,5-bis-O-tert-butyldimethylsilyl-2-deoxy-D-ribo-1,4-lactone

: 122767-57-1
5-O-Benzyl-5-tert-butoxycarbonyl-3-tert-butoxycarbonylamino-2,3-dideoxy-D-ribo-1,4-lactone

Guidance literature:: Multi-step reaction with 8 steps

1: 79 percent / AcOH, H₂O / tetrahydrofuran / 15 h / 30 °C

2: 70 percent / CrO₃, Ac₂O, pyridine / CH₂Cl₂; dimethylformamide / 20 h / Ambient temperature

3: 52 percent / diisobutylaluminium hydride / toluene / 4 h / -78 °C

4: toluene; various solvent(s) / 1.) 0 deg C, 30 min., 2.) RT, 1 h

5: NaH / dimethylformamide / 1.) 0 deg C, 30 min; 2.) RT, 8 h

6: Hg(OAc)2 / tetrahydrofuran; H₂O / 1 h / Ambient temperature

7: n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 18 h / Ambient temperature

8: N-iodosuccinimide, n-BuN₄⁽¹⁺⁾*I^(1-) / CH₂Cl₂

With pyridine; chromium(VI) oxide; N-iodo-succinimide; mercury(II) diacetate; tetrabutyl ammonium fluoride; water; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)82339-4