(3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid

Base Information

• Chemical Name: (3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid
• CAS No.: 191530-30-0
• Molecular Formula: C₂₂H₃₀N₂O₈
• Molecular Weight: 450.489
• Mol file: 191530-30-0.mol

Synonyms:(3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid

Chemical Property of (3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid

There total 3 articles about (3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid 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: 80.0%

(2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol (191530-29-7) → (3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid (191530-30-0)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In tetrachloromethane; acetonitrile; for 0.666667h; Ambient temperature;

DOI:10.1021/jm960627l

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid (191530-30-0)

Guidance literature:

Multi-step reaction with 2 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

With ruthenium(IV) oxide; sodium periodate; N-ethyl-N,N-diisopropylamine; In methanol; tetrachloromethane; 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) → (3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid (191530-30-0)

Guidance literature:

Multi-step reaction with 2 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

With ruthenium(IV) oxide; sodium periodate; N-ethyl-N,N-diisopropylamine; In methanol; tetrachloromethane; acetonitrile;

DOI:10.1021/jm960627l

upstream raw materials:

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

benzyl chloroformate

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

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

C₃₅H₄₉N₅O₉

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