(2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester

Base Information

Chemical Name:(2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester
CAS No.:374753-02-3
Molecular Formula:C₂₇H₄₈O₆Si
Molecular Weight:496.76
Hs Code.:

Synonyms:(2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester

Suppliers and Price of (2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester

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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 (2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester

There total 7 articles about (2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl 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: 76.0%

: 13154-24-0
triisopropylsilyl chloride

: 482626-41-5
(2S,3R,4S,5S)-5-Benzyloxymethoxy-3,7-dihydroxy-2,4-dimethyl-heptanoic acid methyl ester

: 374753-02-3
(2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/ja0279646

Reference yield:

: 152330-77-3
(2R,3S)-3-hydroxy-N-methoxy-5-(4-methoxybenzyloxy)-N,2-dimethylpentanamide

: 374753-02-3
(2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: DIPEA; TBAI / CH₂Cl₂ / 15 h / 20 °C

2.1: DIBAL / tetrahydrofuran / 1 h / -78 °C

3.1: n-Bu₂BOTf; TEA / CH₂Cl₂ / 0.5 h / -40 - 0 °C

3.2: CH₂Cl₂ / 5 h / -78 - 0 °C

4.1: Sm(OTf)3 / 15 h / 20 °C

5.1: CAN / acetonitrile; H₂O / 1 h / 20 °C

6.1: imidazole / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; ammonium cerium(IV) nitrate; di-n-butylboryl trifluoromethanesulfonate; TEA; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ja016272z

Reference yield:

: 129985-91-7
<3(2R,3S),4R,5S>-3-<3-hydroxy-5-<(4-methoxyphenyl)methoxy>-2-methyl-1-oxopentyl>-4-methyl-5-phenyl-2-oxazolidinone

: 374753-02-3
(2S,3R,4S,5S)-5-Benzyloxymethoxy-3-hydroxy-2,4-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: Me₃Al / tetrahydrofuran / 3 h / -20 - 20 °C

2.1: DIPEA; TBAI / CH₂Cl₂ / 15 h / 20 °C

3.1: DIBAL / tetrahydrofuran / 1 h / -78 °C

4.1: n-Bu₂BOTf; TEA / CH₂Cl₂ / 0.5 h / -40 - 0 °C

4.2: CH₂Cl₂ / 5 h / -78 - 0 °C

5.1: Sm(OTf)3 / 15 h / 20 °C

6.1: CAN / acetonitrile; H₂O / 1 h / 20 °C

7.1: imidazole / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; ammonium cerium(IV) nitrate; di-n-butylboryl trifluoromethanesulfonate; TEA; trimethylaluminum; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ja016272z