(2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide

Base Information

Chemical Name:(2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide
CAS No.:137963-56-5
Molecular Formula:C₂₄H₃₂O₄Si
Molecular Weight:412.601
Hs Code.:

Synonyms:(2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide

Chemical Property:

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Technology Process of (2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide

There total 12 articles about (2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide 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: 40.0%

: 137963-58-7
(4S,5R)-6-(tert-butyldiphenylsilyl)oxy-4-methoxy-5-hexanolide

: 74-88-4
methyl iodide

: 137963-57-6
(2S,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide

: 137963-56-5
(2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1016/S0040-4020(96)01138-6

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 137963-56-5
(2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

2: 90 percent / Zn-Cu, KI / dimethylformamide / 4 h / Heating

3: 90 percent / NaH / tetrahydrofuran / 1.) reflux, 30 min, 2.) room temperature, 30 min

4: 92 percent / 4A MS, m-CPBA, BF₃*OEt₂ / CH₂Cl₂ / 1 h / -15 °C

5: 95 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 760 Torr / Ambient temperature

6: 40 percent / LDA, HMPA / tetrahydrofuran / 1 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; boron trifluoride diethyl etherate; hydrogen; copper; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium iodide; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(96)01138-6

Reference yield:

: 22860-24-8
5-hydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl-dimethanesulfonate

: 137963-56-5
(2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

2: 90 percent / Zn-Cu, KI / dimethylformamide / 4 h / Heating

3: 90 percent / NaH / tetrahydrofuran / 1.) reflux, 30 min, 2.) room temperature, 30 min

4: 92 percent / 4A MS, m-CPBA, BF₃*OEt₂ / CH₂Cl₂ / 1 h / -15 °C

5: 95 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 760 Torr / Ambient temperature

6: 40 percent / LDA, HMPA / tetrahydrofuran / 1 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; boron trifluoride diethyl etherate; hydrogen; copper; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium iodide; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(96)01138-6