(1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one

Base Information

Chemical Name:(1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one
CAS No.:383187-60-8
Molecular Formula:C₂₅H₃₄O₇
Molecular Weight:446.541
Hs Code.:

Synonyms:(1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one

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Chemical Property of (1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one

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Technology Process of (1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one

There total 1 articles about (1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one 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: 62.0%

: 85071-59-6
1-bromo-2,3,5-trimethoxy-4-methylbenzaldehyde

: 182193-69-7
(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one

: 383187-60-8
(1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one

Guidance literature:: (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at -78 - -40 ℃;

1-bromo-2,3,5-trimethoxy-4-methylbenzaldehyde; In diethyl ether; at -78 - 15 ℃; for 16h;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

Reference yield:

: 383187-60-8
(1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one

: 383187-63-1
(1R,2R,3S,4S)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentane-1,3-diol

Guidance literature:: With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -30 - 20 ℃; for 16h;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

Reference yield:

: 383187-60-8
(1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one

: 383187-79-9
(2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: Me₄NBH(OAc)3 / acetonitrile; acetic acid / 16 h / -30 - 20 °C

2.1: 93 percent / 18 h / 20 °C

3.1: 83 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂; H₂O; various solvent(s) / 0.5 h

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.75 h / -78 - 0 °C

5.1: LiOH / diethyl ether / 0.25 h / 20 °C

5.2: 85 percent / diethyl ether / 4 h / 20 °C

6.1: 84 percent / aq. HCl / methanol / 6 h / 20 °C

7.1: p-TsNHNH₂; 4 Angstroem molecular sieves / ethanol / 2 h / Heating

7.2: 65 percent / NaCNBH₃; ZnCl₂ / ethanol / 8 h / Heating

With hydrogenchloride; lithium hydroxide; oxalyl dichloride; 4 A molecular sieve; dimethyl sulfoxide; triethylamine; toluene-4-sulfonic acid hydrazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; acetonitrile; 4.1: Swern oxidation / 5.1: Horner-Wadsworth-Emmons reaction / 5.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W