(2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol

Base Information

Chemical Name:(2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol
CAS No.:221695-38-1
Molecular Formula:C₁₄H₂₆N₂O₄
Molecular Weight:286.371
Hs Code.:

Synonyms:(2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol

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Chemical Property of (2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol

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Technology Process of (2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol

There total 11 articles about (2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol 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: 99.0%

: 221695-35-8
(2S,3S,4R,5R)-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methyl-2-phthalimidopiperidine-3,4-diol

: 221695-38-1
(2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol

Guidance literature:: With hydrazine hydrate; In methanol; Ambient temperature;
DOI:10.1016/S0040-4039(99)00184-7

Reference yield:

: 268211-09-2
1-(t-butoxycarbonyl)amino-1,2-dideoxy-3,4-O-isopropylidene-2-methylene-D-erythro-D-pentitol

: 221695-38-1
(2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / DMSP; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 95 percent / Ph₃P; DEAD / dimethylformamide / 20 °C

3: 75 percent / H₂ / Pd/C / methanol / 5 h / 20 °C

4: 99 percent / N₂H₄*H₂O / methanol / 20 °C

With oxalyl dichloride; hydrogen; hydrazine hydrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Cyclization / 2: Substitution / 3: Catalytic hydrogenation / 4: Substitution;
DOI:10.1016/S0968-0896(99)00289-8

Reference yield:

: 221695-30-3
(2R,3R,4S)-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylenepiperidine-2,3,4-triol

: 221695-38-1
(2R,3S,4R,5R)-2-amino-N-(t-butoxycarbonyl)-3,4-O-isopropylidene-5-methylpiperidine-3,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / Ph₃P; DEAD / dimethylformamide / 20 °C

2: 75 percent / H₂ / Pd/C / methanol / 5 h / 20 °C

3: 99 percent / N₂H₄*H₂O / methanol / 20 °C

With hydrogen; hydrazine hydrate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Catalytic hydrogenation / 3: Substitution;
DOI:10.1016/S0968-0896(99)00289-8