2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester
CAS No.:197228-04-9
Molecular Formula:C₂₄H₃₈O₆
Molecular Weight:422.562
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester

There total 10 articles about 2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl 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: 90.0%

: 3282-30-2
pivaloyl chloride

: 197227-75-1
(E)-(3S,4S,5R)-5-Methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-ene-1,3-diol

: 197228-04-9
2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester

Guidance literature:: With pyridine; In dichloromethane;
DOI:10.1016/S0040-4039(97)01605-5

Reference yield:

: 197227-96-6
(E)-(2S,3R)-6-(4-Methoxy-benzyloxy)-2,4-dimethyl-hex-4-ene-1,3-diol

: 197228-04-9
2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / imidazole / CH₂Cl₂

2: NaH / tetrahydrofuran

3: PPTs / ethanol / 66 °C

4: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 to 22 deg C

5: Et₃N, DMSO / CH₂Cl₂ / 22 °C

6: 93 percent / DIBAL / CH₂Cl₂

7: 93 percent / t-BuOOH, Ti(O-i-Pr)4, (-)-DET, CaH₂, 4A sieves / CH₂Cl₂

8: 90 percent / Red-Al / tetrahydrofuran / -78 to 22 deg C

9: 90 percent / pyridine / CH₂Cl₂

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; calcium hydride; oxalyl dichloride; 4 A molecular sieve; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4039(97)01605-5

Reference yield:

: 147438-60-6
(E)-(2R,3R)-3-Methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enal

: 197228-04-9
2,2-Dimethyl-propionic acid (E)-(3S,4S,5R)-3-hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N, DMSO / CH₂Cl₂ / 22 °C

2: 93 percent / DIBAL / CH₂Cl₂

3: 93 percent / t-BuOOH, Ti(O-i-Pr)4, (-)-DET, CaH₂, 4A sieves / CH₂Cl₂

4: 90 percent / Red-Al / tetrahydrofuran / -78 to 22 deg C

5: 90 percent / pyridine / CH₂Cl₂

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; calcium hydride; 4 A molecular sieve; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(97)01605-5