(5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine

Base Information

• Chemical Name: (5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine
• CAS No.: 191530-36-6
• Molecular Formula: C₃₂H₃₄N₂O₇
• Molecular Weight: 558.631

Synonyms:(5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine

Chemical Property of (5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine

Chemical Property:

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Technology Process of (5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine

There total 4 articles about (5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine 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: 70.0%

(3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidene-3-[(diphenylmethoxy)carbonyl]piperidine (191530-34-4) → (5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine (191530-36-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jm960627l

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine (191530-36-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / N,N-diisopropylethylamine / methanol / 1.5 h / 0 °C

2: 80 percent / aq. NaIO₄, RuO₂ / CCl₄; acetonitrile / 0.67 h / Ambient temperature

3: 94 percent / CH₂Cl₂; methanol / Ambient temperature

4: 70 percent / t-BuOK / tetrahydrofuran / 2 h / 0 °C

With ruthenium(IV) oxide; sodium periodate; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; acetonitrile;

DOI:10.1021/jm960627l

Reference yield:

(2S,3R,4S,5R)-2-amino-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-O-isopropylidene-3,4-piperidinediol (176640-82-7) → (5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine (191530-36-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / N,N-diisopropylethylamine / methanol / 1.5 h / 0 °C

2: 80 percent / aq. NaIO₄, RuO₂ / CCl₄; acetonitrile / 0.67 h / Ambient temperature

3: 94 percent / CH₂Cl₂; methanol / Ambient temperature

4: 70 percent / t-BuOK / tetrahydrofuran / 2 h / 0 °C

With ruthenium(IV) oxide; sodium periodate; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; acetonitrile;

DOI:10.1021/jm960627l

upstream raw materials:

(3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidene-3-[(diphenylmethoxy)carbonyl]piperidine

benzyl chloroformate

(2S,3R,4S,5R)-2-amino-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-O-isopropylidene-3,4-piperidinediol

(2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol

Downstream raw materials:

(3aS,4R,7S,7aS)-7-[(benzyloxycarbonyl)amino]-6-N-(tert-butoxycarbonyl)-2-(trichloromethyl)-4-[(diphenylmethoxy)carbonyl]-3a,7a-dihydrooxazolo[5,4-c]piperidine

(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(N,N'-bis(tert-butoxycarbonyl)guanidino)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

(3R,4S,5S,6S)-1-N-(tert-butoxycarbonyl)-4-(N,N'-bis(tert-butoxycarbonyl)guanidino)-6-(trifluoroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

C₃₅H₄₉N₅O₉

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