Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl ester
• CAS No.: 278181-30-9
• Molecular Formula: C₄₀H₆₈O₁₄Si
• Molecular Weight: 801.057

Synonyms:

Chemical Property of Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl ester

There total 24 articles about Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl 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:

1 ,5-pentanediol (111-29-5) → Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl ester (278181-30-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 58 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 45 °C

2.1: 82 percent / PCC / CH₂Cl₂ / 3 h / 20 °C

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

3.2: 68 percent / CH₂Cl₂ / 3 h / -78 - 0 °C

4.1: AlMe₃ / tetrahydrofuran; heptane / 0.42 h / 0 °C

5.1: 636 mg / imidazole / dimethylformamide / 3 h / 0 - 20 °C

6.1: 90 percent / tetrahydrofuran / 3 h / 0 °C

7.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

7.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

8.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C

9.1: 100 percent / HF-pyridine / tetrahydrofuran / 1.25 h / -20 - 0 °C

10.1: 78 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 1 h / -78 °C

11.1: 50 percent / imidazole / dimethylformamide / 3 h / 20 °C

12.1: DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

13.1: 231 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

14.1: HF-pyridine / tetrahydrofuran / 0.5 h / 0 °C

15.1: 71 mg / p-TsOH / 2 h / 20 °C

16.1: Bu₄NF / tetrahydrofuran / 1.5 h / -30 °C

17.1: 22 mg / DMAP; pyridine / 1 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Oxidation / 3.1: Metallation / 3.2: Addition / 4.1: Substitution / 5.1: Substitution / 6.1: Substitution / 7.1: Metallation / 7.2: Addition / 8.1: Acetylation / 9.1: desilylation / 10.1: Reduction / 11.1: Substitution / 12.1: Deacetylation / 13.1: Oxidation / 14.1: desilylation / 15.1: Cyclization / 16.1: desilylation / 17.1: Acetylation;

DOI:10.1021/jo991642b

Reference yield:

5-(4-methoxybenzyloxy)-1-pentanol (131375-63-8) → Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl ester (278181-30-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 82 percent / PCC / CH₂Cl₂ / 3 h / 20 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

2.2: 68 percent / CH₂Cl₂ / 3 h / -78 - 0 °C

3.1: AlMe₃ / tetrahydrofuran; heptane / 0.42 h / 0 °C

4.1: 636 mg / imidazole / dimethylformamide / 3 h / 0 - 20 °C

5.1: 90 percent / tetrahydrofuran / 3 h / 0 °C

6.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

6.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

7.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C

8.1: 100 percent / HF-pyridine / tetrahydrofuran / 1.25 h / -20 - 0 °C

9.1: 78 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 1 h / -78 °C

10.1: 50 percent / imidazole / dimethylformamide / 3 h / 20 °C

11.1: DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

12.1: 231 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

13.1: HF-pyridine / tetrahydrofuran / 0.5 h / 0 °C

14.1: 71 mg / p-TsOH / 2 h / 20 °C

15.1: Bu₄NF / tetrahydrofuran / 1.5 h / -30 °C

16.1: 22 mg / DMAP; pyridine / 1 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; trimethylaluminum; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: Metallation / 2.2: Addition / 3.1: Substitution / 4.1: Substitution / 5.1: Substitution / 6.1: Metallation / 6.2: Addition / 7.1: Acetylation / 8.1: desilylation / 9.1: Reduction / 10.1: Substitution / 11.1: Deacetylation / 12.1: Oxidation / 13.1: desilylation / 14.1: Cyclization / 15.1: desilylation / 16.1: Acetylation;

DOI:10.1021/jo991642b

Reference yield:

5-((4-methoxybenzyl)oxy)pentanal (131375-69-4) → Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl ester (278181-30-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

1.2: 68 percent / CH₂Cl₂ / 3 h / -78 - 0 °C

2.1: AlMe₃ / tetrahydrofuran; heptane / 0.42 h / 0 °C

3.1: 636 mg / imidazole / dimethylformamide / 3 h / 0 - 20 °C

4.1: 90 percent / tetrahydrofuran / 3 h / 0 °C

5.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

6.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C

7.1: 100 percent / HF-pyridine / tetrahydrofuran / 1.25 h / -20 - 0 °C

8.1: 78 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 1 h / -78 °C

9.1: 50 percent / imidazole / dimethylformamide / 3 h / 20 °C

10.1: DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

11.1: 231 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

12.1: HF-pyridine / tetrahydrofuran / 0.5 h / 0 °C

13.1: 71 mg / p-TsOH / 2 h / 20 °C

14.1: Bu₄NF / tetrahydrofuran / 1.5 h / -30 °C

15.1: 22 mg / DMAP; pyridine / 1 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; trimethylaluminum; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Addition / 2.1: Substitution / 3.1: Substitution / 4.1: Substitution / 5.1: Metallation / 5.2: Addition / 6.1: Acetylation / 7.1: desilylation / 8.1: Reduction / 9.1: Substitution / 10.1: Deacetylation / 11.1: Oxidation / 12.1: desilylation / 13.1: Cyclization / 14.1: desilylation / 15.1: Acetylation;

DOI:10.1021/jo991642b

upstream raw materials:

1 ,5-pentanediol

5-(4-methoxybenzyloxy)-1-pentanol

5-((4-methoxybenzyl)oxy)pentanal

p-methoxybenzyl chloride

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