methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate

Base Information

Chemical Name:methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate
CAS No.:95513-72-7
Molecular Formula:C₂₁H₃₀O₆
Molecular Weight:378.466
Hs Code.:

Synonyms:methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate

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Technology Process of methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate

There total 50 articles about methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate 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: 87.0%

: 95513-99-8
methyl (2RS,3SR,4SR,5RS,6RS)-6-O-benzyl-3,5-O-isopropylidene-3,5,6,7-tetrahydroxy-2,4,6-trimethylheptanoate

: 95513-72-7
methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -50 ℃; for 0.75h;
DOI:10.1021/jo00212a018

Reference yield:

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

: 95513-72-7
methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate

Guidance literature:: Multi-step reaction with 9 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

6: pyridinium dichromate / dimethylformamide / 16 h / Ambient temperature

7: diethyl ether / Ambient temperature

8: 96 percent / potassium hydroxide / methanol / 0.75 h / Ambient temperature

9: 87 percent / oxalyl chloride, Me₂SO / CH₂Cl₂ / 0.75 h / -50 °C

With pyridine; potassium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; dimethylsulfide; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; ozone; dimethyl sulfoxide; diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
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

: 95513-72-7
methyl (2RS,3SR,4SR,5RS,6SR)-6-O-benzyl-3,5-O-isopropylidene-7-oxo-3,5,6-trihydroxy-2,4,6-trimethylheptanoate

Guidance literature:: Multi-step reaction with 7 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

4: pyridinium dichromate / dimethylformamide / 16 h / Ambient temperature

5: diethyl ether / Ambient temperature

6: 96 percent / potassium hydroxide / methanol / 0.75 h / Ambient temperature

7: 87 percent / oxalyl chloride, Me₂SO / CH₂Cl₂ / 0.75 h / -50 °C

With pyridine; potassium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; dimethylsulfide; ozone; dimethyl sulfoxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00212a018