Propanoic acid, 2,2-dimethyl-, (2Z,4S,5R,6S)-5-hydroxy-2,4,6-trimethyl-7-(phenylmethoxy)-2-heptenyl ester

Base Information

Chemical Name:Propanoic acid, 2,2-dimethyl-, (2Z,4S,5R,6S)-5-hydroxy-2,4,6-trimethyl-7-(phenylmethoxy)-2-heptenyl ester
CAS No.:600737-64-2
Molecular Formula:C22H34O4
Molecular Weight:362.51
Hs Code.:

Synonyms:

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Chemical Property of Propanoic acid, 2,2-dimethyl-, (2Z,4S,5R,6S)-5-hydroxy-2,4,6-trimethyl-7-(phenylmethoxy)-2-heptenyl ester

Chemical Property:

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Technology Process of Propanoic acid, 2,2-dimethyl-, (2Z,4S,5R,6S)-5-hydroxy-2,4,6-trimethyl-7-(phenylmethoxy)-2-heptenyl ester

There total 6 articles about Propanoic acid, 2,2-dimethyl-, (2Z,4S,5R,6S)-5-hydroxy-2,4,6-trimethyl-7-(phenylmethoxy)-2-heptenyl 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: 88.0%

: 3282-30-2
pivaloyl chloride

: 600737-45-9
(Z)-(4S,5R,6S)-7-Benzyloxy-2,4,6-trimethyl-hept-2-ene-1,5-diol

: 600737-64-2
2,2-Dimethyl-propionic acid (Z)-(4S,5R,6S)-7-benzyloxy-5-hydroxy-2,4,6-trimethyl-hept-2-enyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/jo034521r

Reference yield:

: 63930-49-4
(R)-3-(benzyloxy)-2-methylpropan-1-ol

: 600737-64-2
2,2-Dimethyl-propionic acid (Z)-(4S,5R,6S)-7-benzyloxy-5-hydroxy-2,4,6-trimethyl-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

2: 4.72 g / TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

3: 98 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / 0 °C

4: TsOH / tetrahydrofuran; H₂O / 7 h / Heating

5: 1.58 g / lithium borohydride / tetrahydrofuran / 4 h / 0 °C

6: 88 percent / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; oxalyl dichloride; titanium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1: Swern oxidation / 3: Luche reduction / 4: Ferrier rearrangement;
DOI:10.1021/jo034521r

Reference yield:

: 79027-28-4
(2S)-3-(benzyloxy)-2-methylpropanal

: 600737-64-2
2,2-Dimethyl-propionic acid (Z)-(4S,5R,6S)-7-benzyloxy-5-hydroxy-2,4,6-trimethyl-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 4.72 g / TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

2: 98 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / 0 °C

3: TsOH / tetrahydrofuran; H₂O / 7 h / Heating

4: 1.58 g / lithium borohydride / tetrahydrofuran / 4 h / 0 °C

5: 88 percent / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; titanium tetrachloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 2: Luche reduction / 3: Ferrier rearrangement;
DOI:10.1021/jo034521r