[(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

Base Information

• Chemical Name: [(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester
• CAS No.: 625125-33-9
• Molecular Formula: C₂₄H₃₆O₇
• Molecular Weight: 436.546

Synonyms:[(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

Chemical Property of [(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

There total 24 articles about [(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl 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:

acetic acid tert-butyl ester (540-88-5) → [(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester (625125-33-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h

1.2: tetrahydrofuran; hexane / 0.5 h / Heating

2.1: 87.3 g / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol

3.1: camphorsulfonic acid; methanol

4.1: TBAF / tetrahydrofuran

5.1: Et₃N / CH₂Cl₂ / 20 °C

6.1: NaI; NaHCO₃; Na₂SO₃ / butan-2-one / Heating

7.1: Li₂CuCl₄ / tetrahydrofuran

8.1: O₃ / CH₂Cl₂; methanol

8.2: tributylphosphine / CH₂Cl₂; methanol

9.1: LDA / tetrahydrofuran; hexane

9.2: tetrahydrofuran; hexane

10.1: Dess-Martin reagent / CH₂Cl₂ / 20 °C

11.1: 59 percent / aq. HCl / acetonitrile

12.1: CeCl₃ / tetrahydrofuran; diethyl ether / 2 h

12.2: tetrahydrofuran; diethyl ether / 0.08 h

With hydrogenchloride; methanol; sodium tetrahydroborate; cerium(III) chloride; dilithium tetrachlorocuprate; camphor-10-sulfonic acid; diethyl methoxy borane; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; sodium iodide; sodium sulfite; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; butanone; 1.2: Claisen condensation;

DOI:10.1021/ja030316h

Reference yield:

(R)-benzyl glycidol (14618-80-5) → [(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester (625125-33-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium tetrachlorocuprate (II) / tetrahydrofuran / 3 h

2.1: imidazole / dimethylformamide / 0 - 20 °C

3.1: O₃; NaHCO₃ / methanol; CH₂Cl₂

3.2: 51.1 g / dimethyl sulfide / methanol; CH₂Cl₂ / 12 h

4.1: LDA / tetrahydrofuran; hexane

4.2: tetrahydrofuran; hexane

5.1: Dess-Martin reagent / CH₂Cl₂ / 20 °C

6.1: 59 percent / aq. HCl / acetonitrile

7.1: CeCl₃ / tetrahydrofuran; diethyl ether / 2 h

7.2: tetrahydrofuran; diethyl ether / 0.08 h

With 1H-imidazole; hydrogenchloride; cerium(III) chloride; dilithium tetrachlorocuprate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja030316h

Reference yield:

(2R)-1-(benzyloxy)-4-methyl-4-penten-2-ol (604775-07-7) → [(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester (625125-33-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: imidazole / dimethylformamide / 0 - 20 °C

2.1: O₃; NaHCO₃ / methanol; CH₂Cl₂

2.2: 51.1 g / dimethyl sulfide / methanol; CH₂Cl₂ / 12 h

3.1: LDA / tetrahydrofuran; hexane

3.2: tetrahydrofuran; hexane

4.1: Dess-Martin reagent / CH₂Cl₂ / 20 °C

5.1: 59 percent / aq. HCl / acetonitrile

6.1: CeCl₃ / tetrahydrofuran; diethyl ether / 2 h

6.2: tetrahydrofuran; diethyl ether / 0.08 h

With 1H-imidazole; hydrogenchloride; cerium(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja030316h

upstream raw materials:

methyllithium

[(2R,4S,6R,8R)-8-benzyloxymethyl-4-hydroxy-10-oxo-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

acetic acid tert-butyl ester

(R)-benzyl glycidol

Downstream raw materials:

[(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

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