(2RS,3SR,4SR,5RS,6RS)-7-O-acetyl-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanal

Base Information

Chemical Name:(2RS,3SR,4SR,5RS,6RS)-7-O-acetyl-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanal
CAS No.:95513-96-5
Molecular Formula:C₂₂H₃₂O₆
Molecular Weight:392.492
Hs Code.:

Synonyms:

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Chemical Property of (2RS,3SR,4SR,5RS,6RS)-7-O-acetyl-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanal

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Technology Process of (2RS,3SR,4SR,5RS,6RS)-7-O-acetyl-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanal

There total 12 articles about (2RS,3SR,4SR,5RS,6RS)-7-O-acetyl-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanal 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:

: 95587-25-0
(2SR,3RS,4SR)-3-<(triethylsilyl)oxy>-2,4,6-trimethylhept-5-enal

: 95513-96-5
(2RS,3SR,4SR,5RS,6RS)-7-O-acetyl-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanal

Guidance literature:: Multi-step reaction with 5 steps

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

2: 53 percent / H₂SO₄ / 0.25 h / Ambient temperature

3: 48 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 25 °C

4: 95 percent / pyridine / 14 h / Ambient temperature

5: 1.) ozone, 2.) dimethyl sulfide / 1.) methanol, -78 deg C, 2.) methanol, from -78 deg C to RT

With pyridine; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; ozone; diisopropylamine; In tetrahydrofuran;
DOI:10.1021/jo00212a018

Reference yield:

: 95587-29-4
2,6-di-tert-butyl-4-methylphenyl-(2SR,3RS,4SR,5RS,6SR)-2-O-benzyl-3,5-O-isopropylidene-2,3,5-trihydroxy-2,4,6,8-tetramethylnon-7-enoate

: 95513-96-5
(2RS,3SR,4SR,5RS,6RS)-7-O-acetyl-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanal

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / LiAlH₄ / tetrahydrofuran / 72 h / Heating

2: 95 percent / pyridine / 14 h / Ambient temperature

3: 1.) ozone, 2.) dimethyl sulfide / 1.) methanol, -78 deg C, 2.) methanol, from -78 deg C to RT

With pyridine; lithium aluminium tetrahydride; dimethylsulfide; ozone; In tetrahydrofuran;
DOI:10.1021/jo00212a018

Reference yield:

: 95513-86-3
(2SR,3RS,4SR)-3-hydroxy-3,4,6-trimethylhept-5-enal

: 95513-96-5
(2RS,3SR,4SR,5RS,6RS)-7-O-acetyl-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanal

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / pyridine / diethyl ether; acetonitrile / 0.17 h / -50 °C

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

3: 53 percent / H₂SO₄ / 0.25 h / Ambient temperature

4: 48 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 25 °C

5: 95 percent / pyridine / 14 h / Ambient temperature

6: 1.) ozone, 2.) dimethyl sulfide / 1.) methanol, -78 deg C, 2.) methanol, from -78 deg C to RT

With pyridine; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; ozone; diisopropylamine; In tetrahydrofuran; diethyl ether; acetonitrile;
DOI:10.1021/jo00212a018