(12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol

Base Information

• Chemical Name: (12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol
• CAS No.: 479673-26-2
• Molecular Formula: C₅₈H₉₈O₆Si₂
• Molecular Weight: 947.584

Synonyms:(12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol

Chemical Property of (12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol

There total 20 articles about (12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol 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: 65.0%

C45H59O3PSi + (Z)-(2R,3S,4S)-15-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentadec-5-enal (672296-75-2) → (12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol (479673-26-2)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃; for 4.33333h;

Reference yield:

(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one (154919-93-4) → (12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol (479673-26-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: LiBH₄

1.2: PPTS

2.1: 92 percent / DIBAL

3.1: Dess-Martin periodinane

4.1: 85 percent / LDA

5.1: 88 percent / 2,6-lutidine

6.1: 79 percent / DIBAL

7.1: Dess-Martin periodinane

8.1: CrCl₂

8.2: NaH

9.1: 88 percent / HF*pyridine / pyridine

10.1: I₂; PPh₃; imidazole

11.1: NaHMDS

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; lithium borohydride; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triphenylphosphine; lithium diisopropyl amide; In pyridine; 3.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 8.1: Peterson olefination / 8.2: Peterson olefination / 12.1: Wittig reaction;

DOI:10.1021/ol026942l

Reference yield:

(2S)-2-[(4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propan-1-ol (479673-37-5) → (12S, [13S,] [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-13,19-[BIS-(4-METHOXYBENZYLOXY)-12,] 14,20, 22-tetramethylhexacosa-10,15, 23, 25-TETRAEN-1-(TERT-Butyldimethylsilanyl)-ol (479673-26-2)

Guidance literature:

Multi-step reaction with 6 steps

1: I₂; imidazole; PPh₃

2: benzene / Heating

3: 75 percent / NaHMDS

4: 70 percent / DIBAL

5: Dess-Martin periodinane

6: NaHMDS

With 1H-imidazole; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; In benzene; 3: Wittig reaction / 5: Dess-Martin oxidation / 6: Wittig reaction;

DOI:10.1021/ol026942l

upstream raw materials:

(Z)-(2R,3S,4S)-15-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentadec-5-enal

1,10-Decanediol

10-(tert-butyldimethylsilyl)oxydecan-1-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(10Z,15Z,23Z)-(12S,13S,14S,19R,20S,21S,22S)-21-(tert-Butyl-dimethyl-silanyloxy)-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraen-1-ol

(11Z,16Z)-(13S,14S,15S,20R,21S,22S)-14,20-Bis-(4-methoxy-benzyloxy)-13,15,21-trimethyl-22-((Z)-(S)-1-methyl-penta-2,4-dienyl)-oxacyclodocosa-11,16-dien-2-one

(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

(10Z,15Z,23Z)-(12S,13S,14S,19R,20S,21S,22S)-21-(tert-Butyl-dimethyl-silanyloxy)-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

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