2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

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Chemical Name:2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate
CAS No.:95513-90-9
Molecular Formula:C₃₁H₄₂O₅
Molecular Weight:494.671
Hs Code.:

Synonyms:2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

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Chemical Property of 2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

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Technology Process of 2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

There total 9 articles about 2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate 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: 53.0%

: 95513-87-4
2,6-dimethylphenyl (2SR,3RS,4RS,5RS,6SR)-2-O-benzyl-5-O-(triethylsilyl)-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

: 67-64-1
acetone

: 95513-90-9
2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

Guidance literature:: With sulfuric acid; for 0.25h; Ambient temperature;
DOI:10.1021/jo00212a018

Reference yield:

: 141-79-7
4-methyl-pent-3-en-2-one

: 95513-90-9
2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, below -60 deg C, 10 min; 2.)reflux, 6 h.

2: 46 percent / aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

3: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexanes, -78 deg C, 1 h, 2.) 20 min

4: 100 percent / lithium aluminium hydride / diethyl ether / 3 h / 0 °C

5: 100 percent / potassium carbonate / methanol / 0.5 h / Heating

6: 99 percent / sodium periodate / ethanol; H₂O / 0.5 h / 0 °C

7: 79 percent / pyridine / diethyl ether; acetonitrile / 0.17 h / -50 °C

8: 1.) diisopropylamine, n-butyllithium 2.) N,N,N',N'-tetramethylethylenediamine / 1.) THF, hexanes, -78 deg C, 1 h. 2.) -78 deg C, 20 min.

9: 53 percent / H₂SO₄ / 0.25 h / Ambient temperature

With pyridine; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; potassium carbonate; diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetonitrile;
DOI:10.1021/jo00212a018

Reference yield:

: 14690-10-9
(S,R)-2,4-Dimethylpent-3-enal

: 95513-90-9
2,6-dimethylphenyl (2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexanes, -78 deg C, 1 h, 2.) 20 min

2: 100 percent / lithium aluminium hydride / diethyl ether / 3 h / 0 °C

3: 100 percent / potassium carbonate / methanol / 0.5 h / Heating

4: 99 percent / sodium periodate / ethanol; H₂O / 0.5 h / 0 °C

5: 79 percent / pyridine / diethyl ether; acetonitrile / 0.17 h / -50 °C

6: 1.) diisopropylamine, n-butyllithium 2.) N,N,N',N'-tetramethylethylenediamine / 1.) THF, hexanes, -78 deg C, 1 h. 2.) -78 deg C, 20 min.

7: 53 percent / H₂SO₄ / 0.25 h / Ambient temperature

With pyridine; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; potassium carbonate; diisopropylamine; In methanol; diethyl ether; ethanol; water; acetonitrile;
DOI:10.1021/jo00212a018