(3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal

Base Information

Chemical Name:(3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal
CAS No.:313696-72-9
Molecular Formula:C₄₆H₈₂O₁₀Si
Molecular Weight:823.237
Hs Code.:

(3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal

Synonyms:(3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal

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Chemical Property of (3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal

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Technology Process of (3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal

There total 13 articles about (3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 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: 88.0%

: 313696-74-1
(3R,4R,5R)-(E)-4-(para-methoxybenzyloxy)-3,5-dimethyl-6-oxo-1-ol 2,2-dimethyl-1,3-propane acetal

: 313696-73-0
(3S,4S,6S,7R,8S)-1-iodo-4,8-dimethoxy-3,7-dimethyl-6-(tert-butyldimethyl)silyloxy-10-trimethylacetyloxy-dodec-1-ene

: 313696-72-9
(3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal

Guidance literature:: With chromium dichloride; nickel dichloride; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃;
DOI:10.1021/ja002377a

Reference yield:

: 123-11-5
4-methoxy-benzaldehyde

: 313696-72-9
(3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal

Guidance literature:: Multi-step reaction with 7 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

With pyridine; chromium dichloride; dimethylsulfide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; nickel dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 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

: 313696-72-9
(3R,4R,5R,9S,12S,13R,14S)-(E)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-10,14-dimethoxy-4-(para-methoxybenzyloxy)-3,5,9,13-tetramethyl-16-trimethylacetyloxy-hexadec-7-en-1-al 2,2-dimethyl-1,3-propanediol acetal

Guidance literature:: Multi-step reaction with 5 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

With pyridine; chromium dichloride; titanium tetrachloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; ozone; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 4.1: Takai olefination;
DOI:10.1021/ja002377a