ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Base Information

Chemical Name:ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate
CAS No.:870296-61-0
Molecular Formula:C₃₅H₄₄O₁₀Si
Molecular Weight:652.814
Hs Code.:

ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Synonyms:ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

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Chemical Property of ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

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Technology Process of ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

There total 1 articles about ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate 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: 38.0%

: ethyl (1RS,2SR,3SR,4RS,5SR)-3-p-methoxybenzyloxy-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

: 7322-88-5
(S)-acetylmandelic acid

: 870296-61-0
ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1039/b508675b

Reference yield: 97.0%

: 870296-61-0
ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

: 870296-60-9
ethyl (1R,2S,3S,4R,5S)-2,4-dihydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Guidance literature:: With lithium hydroxide; In ethanol; at 20 ℃; for 48h;
DOI:10.1039/b508675b

Reference yield:

: 870296-61-0
ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

: methyl (2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-hydroxy-2-(2-methylpropyl)-3-methyl-1,7-dioxaspiro-[5.5]undec-8-yl}-2-[(5R,6S)-5-methoxy-4-methyl-6-(2-trimethylsilylethoxy)methoxycyclohexa-1,3-dien-1-yl]-6,8-dimethyldeca-2,4,8-trienoate

Guidance literature:: Multi-step reaction with 17 steps

1.1: 97 percent / aq. LiOH / ethanol / 48 h / 20 °C

2.1: 90 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 90 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: 88 percent / pyridine / tetrahydrofuran / 0.08 h

5.1: 75 percent / NMe₄BH(OAc)3; AcOH / acetonitrile / 1 h / 20 °C

6.1: t-BuOOH / CH₂Cl₂ / 3 h / 20 °C

7.1: n-Bu₂SnO / methanol / 24 h / Heating

7.2: 93 percent / tetra-n-butylammonium iodide / benzene / 36 h / Heating

8.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

9.1: 391 mg / aq. NaOH / ethanol / 24 h / 0 °C

10.1: 390 mg / N,N'-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 18 h / 20 °C

11.1: 98 percent / 5,10,15,20-tetraphenyl-21H,23H-porphine; O₂ / CH₂Cl₂; methanol / 0.67 h / -78 °C / Irradiation

12.1: LHMDS / hexane; tetrahydrofuran / 3 h / -78 - -10 °C

13.1: diethyl ether / 0.33 h / 20 °C

14.1: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 13 h / 20 °C

15.1: Et₃N / xylene / 44 h / 20 °C

16.1: 7.5 mg / DMAP / xylene / 2 h / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; lithium hydroxide; sodium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; oxygen; 5,15,10,20-tetraphenylporphyrin; di(n-butyl)tin oxide; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; acetonitrile; xylene; 2.1: Swern oxidation / 4.1: Swern oxidation / 13.1: Wittig reaction;
DOI:10.1039/b508675b