2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Base Information

Chemical Name:2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione
CAS No.:197087-12-0
Molecular Formula:C₅₁H₅₀Cl₃NO₁₁
Molecular Weight:959.317
Hs Code.:

2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Synonyms:2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

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Chemical Property of 2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

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Technology Process of 2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

There total 6 articles about 2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione 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: 81.0%

: 197087-09-5
2-{(2R,4aR,6R,7R,8R,8aS)-6-Allyloxy-2-phenyl-8-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-isoindole-1,3-dione

: 197087-12-0
2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Guidance literature:: With 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(97)01670-5

Reference yield:

: 104-83-6
1-Chloro-4-(chloromethyl)benzene

: 197087-12-0
2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / NaH, Bu₄NI / dimethylformamide

2: AcOH, 3.0 M H₂SO₄ / 85 °C

3: Et₃N / CH₂Cl₂

4: 90 percent / TfOH / tetrahydrofuran; diethyl ether

5: 81 percent / NaCNBH₃, mol sieves 3A / tetrahydrofuran

With trifluorormethanesulfonic acid; 3 A molecular sieve; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)01670-5

Reference yield:

: 152554-45-5
β-methyl 2,3,4-tri-O-(4-chlorobenzyl)-6-deoxy-L-galactopyranoside

: 197087-12-0
2-{(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-5-hydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-tris-(4-chloro-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 4 steps

1: AcOH, 3.0 M H₂SO₄ / 85 °C

2: Et₃N / CH₂Cl₂

3: 90 percent / TfOH / tetrahydrofuran; diethyl ether

4: 81 percent / NaCNBH₃, mol sieves 3A / tetrahydrofuran

With trifluorormethanesulfonic acid; 3 A molecular sieve; sulfuric acid; sodium cyanoborohydride; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(97)01670-5