(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

Base Information

Chemical Name:(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
CAS No.:1054653-75-6
Molecular Formula:C₅₁H₄₉NO₇
Molecular Weight:787.953
Hs Code.:

Synonyms:

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Chemical Property of (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

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Technology Process of (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

There total 9 articles about (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 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:

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

: 1054653-75-6
(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

Guidance literature:: Multi-step reaction with 9 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

9: aq. OsO₄; NaIO₄ / acetone; 2-methyl-propan-2-ol / 3 h

With sodium periodate; osmium(VIII) oxide; 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; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1039/b206623h

Reference yield:

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 1054653-75-6
(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

Guidance literature:: Multi-step reaction with 2 steps

1: 1.035 g / DIPEA / acetonitrile / 2 h

2: aq. OsO₄; NaIO₄ / acetone; 2-methyl-propan-2-ol / 3 h

With sodium periodate; osmium(VIII) oxide; N-ethyl-N,N-diisopropylamine; In acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1039/b206623h

Reference yield:

: 166111-63-3
N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine

: 1054653-75-6
(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

Guidance literature:: Multi-step reaction with 8 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

8: aq. OsO₄; NaIO₄ / acetone; 2-methyl-propan-2-ol / 3 h

With sodium periodate; osmium(VIII) oxide; 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; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1039/b206623h