{(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol

Base Information

• Chemical Name: {(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol
• CAS No.: 263138-39-2
• Molecular Formula: C₃₂H₅₆O₁₀
• Molecular Weight: 600.791

Synonyms:{(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol

Chemical Property of {(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol

Chemical Property:

Purity/Quality:

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Technology Process of {(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol

There total 19 articles about {(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol 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: 91.0%

(E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-en-1-ol (263138-38-1) → {(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol (263138-39-2)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate; In decane; dichloromethane; at -20 ℃; for 16h;

DOI:10.1021/jo991689x

Reference yield:

(2S,3R,4R)-(+)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-hexyn-3-ol (263138-21-2) → {(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol (263138-39-2)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 96 percent / i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 48 h / 20 °C

2.1: (c-C₆H₁₁)2BH / 1,2-dimethoxy-ethane / 6.5 h / 20 °C

2.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

3.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

4.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

5.1: 71 percent / Bu₄NF / tetrahydrofuran / 24 h / 20 °C

6.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h

7.1: BuLi / tetrahydrofuran; hexane / -78 - -40 °C

7.2: 43 percent / LiBr / tetrahydrofuran; hexane / 1 h / -35 °C

8.1: 59 percent / i-PrO₂CN=NCO₂-i-Pr; Ph₃P / benzene / 18 h / 20 °C

9.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h

10.1: 95 percent / TsNHNH₂; NaOAc / 1,2-dimethoxy-ethane; H₂O / Heating

11.1: 99 percent / i-PrNEt₂; Bu₄NI / CH₂Cl₂ / 42 h / 20 °C

12.1: 96 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

13.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

14.1: 99 percent / CH₂Cl₂ / 20 h / Heating

15.1: 93 percent / DIBAL-H / CH₂Cl₂; various solvent(s) / 0.67 h

16.1: 91 percent / t-BuOOH; Ti(O-i-Pr)4; (-)-i-Pr tartrate / CH₂Cl₂; decane / 16 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; 15-crown-5; N,N-diethyl-N-isopropylamine; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; decane; hexane; dichloromethane; water; benzene; 1.1: Etherification / 2.1: Addition / 2.2: Oxidation / 3.1: Reduction / 4.1: Etherification / 5.1: Hydrolysis / 6.1: Oxidation / 7.1: Metallation / 7.2: Addition / 8.1: Esterification / 9.1: Hydrolysis / 10.1: Hydrogenation / 11.1: Etherification / 12.1: Hydrolysis / 13.1: Oxidation / 14.1: Condensation / 15.1: Reduction / 16.1: Oxidation;

DOI:10.1021/jo991689x

Reference yield:

(2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-3-methoxymethoxy-5-hexyne (263138-22-3) → {(2R,3R)-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-Methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxiranyl}-methanol (263138-39-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: (c-C₆H₁₁)2BH / 1,2-dimethoxy-ethane / 6.5 h / 20 °C

1.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

2.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

3.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

4.1: 71 percent / Bu₄NF / tetrahydrofuran / 24 h / 20 °C

5.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h

6.1: BuLi / tetrahydrofuran; hexane / -78 - -40 °C

6.2: 43 percent / LiBr / tetrahydrofuran; hexane / 1 h / -35 °C

7.1: 59 percent / i-PrO₂CN=NCO₂-i-Pr; Ph₃P / benzene / 18 h / 20 °C

8.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h

9.1: 95 percent / TsNHNH₂; NaOAc / 1,2-dimethoxy-ethane; H₂O / Heating

10.1: 99 percent / i-PrNEt₂; Bu₄NI / CH₂Cl₂ / 42 h / 20 °C

11.1: 96 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

12.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

13.1: 99 percent / CH₂Cl₂ / 20 h / Heating

14.1: 93 percent / DIBAL-H / CH₂Cl₂; various solvent(s) / 0.67 h

15.1: 91 percent / t-BuOOH; Ti(O-i-Pr)4; (-)-i-Pr tartrate / CH₂Cl₂; decane / 16 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; 15-crown-5; N,N-diethyl-N-isopropylamine; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; Dess-Martin periodane; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; decane; hexane; dichloromethane; water; benzene; 1.1: Addition / 1.2: Oxidation / 2.1: Reduction / 3.1: Etherification / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Esterification / 8.1: Hydrolysis / 9.1: Hydrogenation / 10.1: Etherification / 11.1: Hydrolysis / 12.1: Oxidation / 13.1: Condensation / 14.1: Reduction / 15.1: Oxidation;

DOI:10.1021/jo991689x

upstream raw materials:

(E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-en-1-ol

p-methoxybenzyl chloride

(2S,3R,4R)-(+)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-hexyn-3-ol

(2R,3S,4S)-1-(tert-butyldiphenylsilyloxy)-2,4-dimethyl-5-hexyn-3-ol

Downstream raw materials:

(3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol

(2S,3R)-2-Iodomethyl-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxirane

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