(3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one

Base Information

• Chemical Name: (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one
• CAS No.: 292062-92-1
• Molecular Formula: C₅₉H₅₇NO₇
• Molecular Weight: 892.104
• Mol file: 292062-92-1.mol

Synonyms:(3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one

Chemical Property of (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one

There total 5 articles about (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one 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: 90.0%

(2R,3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-ol → (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one (292062-92-1)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 24h;

DOI:10.1039/b206623h

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one (292062-92-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / p-TsOH; 4 Angstroem molecular sieves / CH₂Cl₂

2: diethyl ether

3: 97 percent / DIPEA / acetonitrile / 5 h

4: 90 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 24 h

With 4 A molecular sieve; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1039/b206623h

Reference yield:

N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine (166111-63-3) → (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one (292062-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether

2: 97 percent / DIPEA / acetonitrile / 5 h

3: 90 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 24 h

With 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1039/b206623h

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine

benzylamine

Downstream raw materials:

(2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-N-(fluoren-9-ylmethoxycarbonyl)-6-(prop-2-enyl)piperidine

(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

(2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine

(2R,3R,4R,5S,6R)-N-benzyl-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-6-(prop-2-enyl)piperidine