(3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal

Base Information

• Chemical Name: (3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal
• CAS No.: 262279-34-5
• Molecular Formula: C₄₁H₇₂O₉Si
• Molecular Weight: 737.103
• Mol file: 262279-34-5.mol

Synonyms:(3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal

Chemical Property of (3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal

There total 17 articles about (3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal 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:

(3S,4R,5S,7S,8S,12S,13R,14R)-5-(tert-Butyl-dimethyl-silanyloxy)-15-(5,5-dimethyl-[1,3]dioxan-2-yl)-3,7-dimethoxy-13-(4-methoxy-benzyloxy)-4,8,12,14-tetramethyl-pentadecane-1,11-diol → (3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal (262279-34-5)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ja994003r

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal (262279-34-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / p-toluene sulfonic acid monohydrade / benzene / 20 h / 25 °C

2: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 15 h / -50 °C

3: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

4: LDA / tetrahydrofuran; hexane / 0.5 h / -10 °C

5: 2.75 g / PPTS / benzene / 5 h / Heating

6: 77 percent / O₃; pyridine; methyl sulfide / methanol; CH₂Cl₂ / 15 h / -78 - 25 °C

7: 88 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 20 °C

8: NaNO₂; H₂ / PtO₂ / ethyl acetate; ethanol / 3 h / 3040.2 Torr

9: DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

10: 411 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; chromium dichloride; dimethylsulfide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; nickel dichloride; lithium diisopropyl amide; sodium nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; benzene;

DOI:10.1021/ja002377a

Reference yield:

2,2-Dimethyl-propionic acid (3S,4R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4-methyl-7-oxo-heptyl ester → (3R,4R,5R,9S,10S,12S,13R,14S)-12-(tert-butyldimethylsilyloxy)-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-6,16-dioxo-1-hexadecanal 2,2-dimethyl-1,3-propanediol acetal (262279-34-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 88 percent / TiCl₄ / CH₂Cl₂ / 8 h / -78 °C

2.1: 87 percent / Proton Sponge(R) / CH₂Cl₂ / 15 h / 0 - 25 °C

3.1: O₃; pyridine / methanol / 0.17 h / -78 °C

3.2: methylsulfide / methanol / 10 h / 25 °C

4.1: 1.18 g / CrCl₂ / tetrahydrofuran / 20 °C

5.1: 88 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 20 °C

6.1: NaNO₂; H₂ / PtO₂ / ethyl acetate; ethanol / 3 h / 3040.2 Torr

7.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

8.1: 411 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; chromium dichloride; hydrogen; titanium tetrachloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; Dess-Martin periodane; ozone; nickel dichloride; sodium nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; 4.1: Takai olefination;

DOI:10.1021/ja002377a

upstream raw materials:

4-methoxy-benzaldehyde

(5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene

(5S,6S,8S,9R,10S)-6-hydroxy-10-methoxy-5,9-dimethyl-8-(tert-butyldimethyl)silyloxy-12-trimethylacetyloxy-dodec-3-ene

(3S,4S,6S,7R,8S)-1-iodo-4,8-dimethoxy-3,7-dimethyl-6-(tert-butyldimethyl)silyloxy-10-trimethylacetyloxy-dodec-1-ene

Downstream raw materials:

C₆₃H₈₂N₄O₁₄Si

C₇₂H₁₀₅N₃O₁₆Si₂

9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid

C₆₆H₈₉N₃O₁₅Si