(4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

Base Information

• Chemical Name: (4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one
• CAS No.: 871236-70-3
• Molecular Formula: C₅₈H₈₂O₆Si₂
• Molecular Weight: 931.456

Synonyms:(4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

Chemical Property of (4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

Chemical Property:

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Technology Process of (4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

There total 26 articles about (4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one 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: 98.0%

(3S,4S,E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide (871236-69-0) → (4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one (871236-70-3)

Guidance literature:

[(2R,4R,5R,6S)-5-(4-methoxybenzyloxy)-2,4,6-trimethyloct-7-ynyloxy](tert-butyl)dimethylsilane; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 0.583333h;

(3S,4S,E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide; In tetrahydrofuran; at -78 - 0 ℃; for 1.08333h;

Reference yield: 98.0%

[(2R,4R,5R,6S)-5-(4-methoxybenzyloxy)-2,4,6-trimethyloct-7-ynyloxy](tert-butyl)dimethylsilane (871236-68-9) + (3S,4S,E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide (871236-69-0) → (4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one (871236-70-3)

Guidance literature:

[(2R,4R,5R,6S)-5-(4-methoxybenzyloxy)-2,4,6-trimethyloct-7-ynyloxy](tert-butyl)dimethylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃;

(3S,4S,E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide; In tetrahydrofuran; hexane; at -78 - 0 ℃; Further stages.;

DOI:10.1016/j.tet.2007.05.033

Reference yield:

(3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol (871237-03-5) → (4S,5S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one (871236-70-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

2.1: NaH₂PO₄*H₂O; NaClO₂; 2-methyl-2-butene / tetrahydrofuran; H₂O / 2 h

3.1: 0.37 g / Et₃N; 4-(dimethylamino)pyridine; DCC / CH₂Cl₂ / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

4.2: 98 percent / tetrahydrofuran; hexane / -78 - 0 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; 1.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2007.05.033

upstream raw materials:

[(2R,4R,5R,6S)-5-(4-methoxybenzyloxy)-2,4,6-trimethyloct-7-ynyloxy](tert-butyl)dimethylsilane

(3S,4S,E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide

(2R,3S)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylpentanal

C₇H₁₄O₂

Downstream raw materials:

(4S,5S,7S,10S,11R,12R,14R,E)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-ol

(2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

(2E,4S,5S,7S,8Z,10S,11R,12R,14R)-11-(4-methoxybenzyloxy)-5,15-bis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadeca-2,8-dien-7-ol

[(2E,4S,5S,7S,8Z,10S,11R,12R,14R)-11-(4-methoxybenzyloxy)-5,7,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethylpentadeca-2,8-dienyloxy]triphenylmethane

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