(S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol

Base Information

• Chemical Name: (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol
• CAS No.: 94944-61-3
• Molecular Formula: C₂₅H₃₃NO₇S
• Molecular Weight: 491.606
• Mol file: 94944-61-3.mol

Synonyms:

Chemical Property of (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol

There total 5 articles about (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol 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%

3,4-dihydro-2H-pyran (110-87-2) + (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-5-amino-1,2-pentanediol (94944-66-8) → (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol (94944-61-3,94944-67-9)

Guidance literature:

With toluene-4-sulfonic acid; In diethyl ether; Ambient temperature;

DOI:10.1021/jo00206a040

Reference yield:

(S)-4,5-O-isopropylidene-4,5-dihydroxypentanenitrile (94944-62-4) → (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol (94944-61-3,94944-67-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating

2: 93 percent / magnesium oxide / H₂O / 3 h / 0 °C

3: 60 percent / 90percent aq. trifluoroacetic acid / 0.08 h / Ambient temperature

4: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 8 deg C, 40 h

5: 100 percent / 4-methylbenzenesulfonic acid / diethyl ether / Ambient temperature

With pyridine; lithium aluminium tetrahydride; magnesium oxide; toluene-4-sulfonic acid; trifluoroacetic acid; In diethyl ether; water;

DOI:10.1021/jo00206a040

Reference yield:

(S)-1,2-O-isopropylidene-5-amino-1,2-pentanediol (94944-63-5) → (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol (94944-61-3,94944-67-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / magnesium oxide / H₂O / 3 h / 0 °C

2: 60 percent / 90percent aq. trifluoroacetic acid / 0.08 h / Ambient temperature

3: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 8 deg C, 40 h

4: 100 percent / 4-methylbenzenesulfonic acid / diethyl ether / Ambient temperature

With pyridine; magnesium oxide; toluene-4-sulfonic acid; trifluoroacetic acid; In diethyl ether; water;

DOI:10.1021/jo00206a040

upstream raw materials:

3,4-dihydro-2H-pyran

(S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-5-amino-1,2-pentanediol

(S)-4,5-O-isopropylidene-4,5-dihydroxypentanenitrile

(S)-1,2-O-isopropylidene-5-amino-1,2-pentanediol

Downstream raw materials:

(S)-N-<(benzyloxy)carbonyl>-3-O-(2-tetrahydropyranyl)-3-piperidinol

(S)-3-hydroxypiperidine

(S)-3-hydroxypiperidine-N-carboxylate benzyl ester