(4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

Base Information

• Chemical Name: (4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol
• CAS No.: 861822-08-4
• Molecular Formula: C₅₅H₉₀O₅Si₃
• Molecular Weight: 915.573
• Mol file: 861822-08-4.mol

Synonyms:(4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

Chemical Property of (4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

There total 14 articles about (4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-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: 71.0%

((2E,4R,5S,7S,8Z,10S,11R,12S)-5,7,11,15-tetrakis(tert-butyldimethylsilyloxy)-4,10,12-trimethylpentadeca-2,8-dienyloxy)triphenylmethane (861822-07-3) → (4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol (861822-08-4)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 0 ℃; for 24h;

DOI:10.1021/ol050808u

Reference yield: 71.0%

→ (4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol (861822-08-4)

Guidance literature:

Reference yield:

(3S,4R,5S)-4,8-bis(tert-butyldimethylsilyloxy)-3,5-dimethyloct-1-yne (861821-96-7) → (4S,5R,6S,7Z,9S,11S,12R,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-4,6,12-trimethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol (861822-08-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / n-butyllithium

2: 95 percent / (S,S)-Noyori catalyst / propan-2-ol

3: 100 percent / H₂ / Lindlar catalyst / toluene

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5: 71 percent / HF*pyridine; pyridine / tetrahydrofuran / 21 h / 0 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; hydrogen; pyridine hydrogenfluoride; Lindlar's catalyst; (S,S)-Noyori catalyst; In tetrahydrofuran; dichloromethane; isopropyl alcohol; toluene; 3: Lindlar hydrogenation;

DOI:10.1021/jm061385k

upstream raw materials:

((2E,4R,5S,7S,8Z,10S,11R,12S)-5,7,11,15-tetrakis(tert-butyldimethylsilyloxy)-4,10,12-trimethylpentadeca-2,8-dienyloxy)triphenylmethane

(2S,3R,4S)-3,7-bis(tert-butyldimethylsilyloxy)-2,4-dimethylheptan-1-ol

(3S,4R,5S)-4,8-bis(tert-butyldimethylsilyloxy)-3,5-dimethyloct-1-yne

(4S,5R,6S)-7-(methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptan-1-ol

Downstream raw materials:

(2R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-3-one

(2S,3R,8S,9R,10S,11Z,13S,15S,16R,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol

(4S,5S)-4-((2R,3R,8S,9R,10S,11Z,13S,15S,16R,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-8,10,16-trimethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

(2R,4E,8S,9R,10S,11Z,13S,15S,16R,17E)-9,15-bis(tert-butyldimethylsilyloxy)-13-(tert-butyldimethylsilyloxy)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-8,10,16-trimethyl-19-(trityloxy)nonadeca-4,11,17-trien-3-one