ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate

Base Information

Chemical Name:ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate
CAS No.:502506-92-5
Molecular Formula:C₃₅H₄₄Cl₄O₆Si
Molecular Weight:730.628
Hs Code.:

Synonyms:ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate

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Chemical Property of ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate

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Technology Process of ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate

There total 13 articles about ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate 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: 52.0%

: 502506-90-3
ethyl (2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)pent-4-enoate

: 502506-91-4
(2S,3R,4S)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-4-methyl-δ-valerolactone

: 502506-92-5
ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate

Guidance literature:: ethyl (2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)pent-4-enoate; With Wilkinson's catalyst; hydrogen; In benzene; for 4h; under 11250.9 Torr;

With trifluoroacetic acid; In chloroform; for 0.166667h;
DOI:10.1016/S0040-4020(02)01451-5

Reference yield:

: 102-47-6
3,4-Dichlorophenylmethyl chloride

: 502506-92-5
ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 67 percent / K₂CO₃; KI / dimethylformamide / 10 h / Heating

2.1: 81 percent / SnCl₄ / CH₂Cl₂ / 22 h / -47 °C

3.1: 81 percent / KOH / ethanol; 1,2-dimethoxy-ethane; H₂O / 20 h / 65 °C

4.1: 83 percent / SOCl₂ / dimethylformamide / 6 h / 20 °C

5.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 20 °C

6.1: 4 percent / SeO₂; tert-butyl hydroperoxide / various solvent(s); CH₂Cl₂ / 48 h

7.1: 97 mg / NaBH₄ / methanol / 0.5 h / -15 °C

8.1: ((C₆H₅)3P)RhCl; H₂ / benzene / 4 h / 11250.9 Torr

8.2: 14 percent / trifluoroacetic acid / CHCl₃ / 0.17 h

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; selenium(IV) oxide; thionyl chloride; hydrogen; tin(IV) chloride; potassium carbonate; potassium iodide; In methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(02)01451-5

Reference yield:

: 488-17-5
3-methylbenzene-1,2-diol

: 502506-92-5
ethyl (2S,3R,4R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4-methylpent-4-enoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 90 percent / NaH / dimethylformamide; methanol / 0.5 h / 0 °C

2.1: n-C₄H₉Li / tetrahydrofuran; hexane / 2 h / 0 - 20 °C

2.2: 96 percent / tetrahydrofuran; hexane / 1 h / 0 °C

3.1: n-C₄H₉Li / tetrahydrofuran; hexane / 1 h / 0 °C

3.2: 87 percent / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

4.1: 99 percent / HCl / ethyl acetate / 0.75 h

5.1: 67 percent / K₂CO₃; KI / dimethylformamide / 10 h / Heating

6.1: 81 percent / SnCl₄ / CH₂Cl₂ / 22 h / -47 °C

7.1: 81 percent / KOH / ethanol; 1,2-dimethoxy-ethane; H₂O / 20 h / 65 °C

8.1: 83 percent / SOCl₂ / dimethylformamide / 6 h / 20 °C

9.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 20 °C

10.1: 4 percent / SeO₂; tert-butyl hydroperoxide / various solvent(s); CH₂Cl₂ / 48 h

11.1: 97 mg / NaBH₄ / methanol / 0.5 h / -15 °C

12.1: ((C₆H₅)3P)RhCl; H₂ / benzene / 4 h / 11250.9 Torr

12.2: 14 percent / trifluoroacetic acid / CHCl₃ / 0.17 h

With 2,6-dimethylpyridine; hydrogenchloride; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; selenium(IV) oxide; thionyl chloride; hydrogen; tin(IV) chloride; sodium hydride; potassium carbonate; potassium iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene; 3.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)01451-5