1-Piperidinecarboxylic acid, 3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-(2-propenyl)-, 9H-fluoren-9-ylmethyl ester, (2R,3R,4R,5S,6R)-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-(2-propenyl)-, 9H-fluoren-9-ylmethyl ester, (2R,3R,4R,5S,6R)-
• CAS No.: 497931-28-9
• Molecular Formula: C₅₂H₅₁NO₆
• Molecular Weight: 785.98
• Mol file: 497931-28-9.mol

Synonyms:

Chemical Property of 1-Piperidinecarboxylic acid, 3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-(2-propenyl)-, 9H-fluoren-9-ylmethyl ester, (2R,3R,4R,5S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-(2-propenyl)-, 9H-fluoren-9-ylmethyl ester, (2R,3R,4R,5S,6R)-

There total 8 articles about 1-Piperidinecarboxylic acid, 3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-(2-propenyl)-, 9H-fluoren-9-ylmethyl ester, (2R,3R,4R,5S,6R)- 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:

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) → (2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-N-(fluoren-9-ylmethoxycarbonyl)-6-(prop-2-enyl)piperidine (497931-28-9)

Guidance literature:

Multi-step reaction with 8 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

5: Et₂NH / acetonitrile / 2 h

6: NaBH(OAc)3; Na₂SO₄; glac. AcOH / 1,2-dichloro-ethane / 24 h

7: aq. ammonium cerium(IV) nitrate / tetrahydrofuran

8: 1.035 g / DIPEA / acetonitrile / 2 h

With ammonium cerium(IV) nitrate; 4 A molecular sieve; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; acetic acid; sodium sulfate; diethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1039/b206623h

Reference yield:

N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine (166111-63-3) → (2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-N-(fluoren-9-ylmethoxycarbonyl)-6-(prop-2-enyl)piperidine (497931-28-9)

Guidance literature:

Multi-step reaction with 7 steps

1: diethyl ether

2: 97 percent / DIPEA / acetonitrile / 5 h

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

4: Et₂NH / acetonitrile / 2 h

5: NaBH(OAc)3; Na₂SO₄; glac. AcOH / 1,2-dichloro-ethane / 24 h

6: aq. ammonium cerium(IV) nitrate / tetrahydrofuran

7: 1.035 g / DIPEA / acetonitrile / 2 h

With ammonium cerium(IV) nitrate; 4 A molecular sieve; sodium tris(acetoxy)borohydride; acetic acid; sodium sulfate; diethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1039/b206623h

Reference yield:

(2R,3R,4R,5S,6R)-N-benzyl-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-6-(prop-2-enyl)piperidine (292062-93-2) → (2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-N-(fluoren-9-ylmethoxycarbonyl)-6-(prop-2-enyl)piperidine (497931-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. ammonium cerium(IV) nitrate / tetrahydrofuran

2: 1.035 g / DIPEA / acetonitrile / 2 h

With ammonium cerium(IV) nitrate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1039/b206623h

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

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

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

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