(3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine

Base Information

Chemical Name:(3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine
CAS No.:226988-18-7
Molecular Formula:C₂₈H₃₂N₂O₄
Molecular Weight:460.573
Hs Code.:

Synonyms:(3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine

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Chemical Property of (3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine

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Technology Process of (3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine

There total 5 articles about (3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine 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:

: Methanesulfonic acid (1R,2R,3S)-4-(N-acetyl-hydrazino)-2,3-bis-benzyloxy-1-benzyloxymethyl-butyl ester

: 226988-18-7
(3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In nitromethane; at 60 ℃; for 18h; Yield given;
DOI:10.1055/s-1999-2716

Reference yield:

: 16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3
2,3,5-tri-O-benzyl-D-xylofuranose

: 226988-18-7
(3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / AcOH; NaCNBH₃ / methanol / 18 h / 60 °C

2: methanol / 18 h

3: 229 mg / pyridine / 1 h / 0 - 20 °C

4: TFA / 1 h / 20 °C

5: 115 mg / i-Pr₂NEt / nitromethane / 18 h / 60 °C

With pyridine; sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; nitromethane; 1: Substitution / 2: Acetylation / 3: Substitution / 4: Substitution / 5: Cyclization;
DOI:10.1002/(SICI)1521-3765(20000117)6:2<278::AID-CHEM278>3.0.CO;2-6

Reference yield:

: 226988-16-5
N'-acetyl-N'-(2,3,5-tris-benzyloxy-4-hydroxy-pentyl)-hydrazinecarboxylic acid tert-butyl ester

: 226988-18-7
(3S,4S,5S)-1-N-Acetyl-3',4,5-tri-O-benzyl-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine

Guidance literature:: Multi-step reaction with 3 steps

1: 229 mg / pyridine / 1 h / 0 - 20 °C

2: TFA / 1 h / 20 °C

3: 115 mg / i-Pr₂NEt / nitromethane / 18 h / 60 °C

With pyridine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In nitromethane; 1: Substitution / 2: Substitution / 3: Cyclization;
DOI:10.1002/(SICI)1521-3765(20000117)6:2<278::AID-CHEM278>3.0.CO;2-6