(E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic acid methyl ester

Base Information

Chemical Name:(E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic acid methyl ester
CAS No.:146980-53-2
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

Synonyms:(E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic 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 (E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic acid methyl ester

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Technology Process of (E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic acid methyl ester

There total 12 articles about (E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic 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: 83.0%

: 1027600-45-8
((2R,3S,4R,5S)-5-Benzyloxymethyl-3,4-dimethyl-3-trimethylsilanyl-tetrahydro-furan-2-yl)-acetic acid methyl ester

: 146980-53-2
(E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic acid methyl ester

Guidance literature:: tin(IV) chloride; at -35 ℃;
DOI:10.1021/jo00057a007

Reference yield:

: 497-02-9
(E)-2-methyl-2-buten-1-ol

: 146980-53-2
(E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C

2: t-BuLi / -78 deg C to -35 deg C, 8 h

3: NEt₃ / DMAP / CH₂Cl₂

4: 1.) BF₃*OEt₂, 2.) LiAlH₄ / 1.) 0 deg C to r.t., 1 h, 2.) THF

5: pentane / 10 h / Ambient temperature; Lipase Amano-AK

6: LiAlH₄ / tetrahydrofuran

7: propionic acid / toluene / Heating

8: SnCl₄ / CH₂Cl₂ / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; boron trifluoride diethyl etherate; tert.-butyl lithium; triethylamine; dmap; tin(IV) chloride; propionic acid; In tetrahydrofuran; dichloromethane; toluene; pentane;
DOI:10.1021/jo00057a007

Reference yield:

: 146980-54-3
(E)-2-Methyl-1-trimethylsilanyl-but-2-en-1-ol

: 146980-53-2
(E)-(5S,6S)-7-Benzyloxy-6-hydroxy-4,5-dimethyl-hept-3-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NEt₃ / DMAP / CH₂Cl₂

2: 1.) BF₃*OEt₂, 2.) LiAlH₄ / 1.) 0 deg C to r.t., 1 h, 2.) THF

3: pentane / 10 h / Ambient temperature; Lipase Amano-AK

4: LiAlH₄ / tetrahydrofuran

5: propionic acid / toluene / Heating

6: SnCl₄ / CH₂Cl₂ / -78 °C

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; triethylamine; dmap; tin(IV) chloride; propionic acid; In tetrahydrofuran; dichloromethane; toluene; pentane;
DOI:10.1021/jo00057a007